Vacation Home Rentals By Owner In Gulfport, FL

$349.14

House of Sirenity: Mid Century Beach Bungalow in Artsy Gulfport!

Gulfport, Florida, United States

This is a private one family home located in Gulfport Florida. Gulfport is a lovely artisan town, with a laid back beach vibe. The house is convenient to all St. Pete Beaches and attractions. We are three blocks from Beach Blvd and Boca Ciega Bay Beach. On Beach Blvd you will find lots of restaurants and shops. There is a lovely walking trail and pond across the street. Nearby you can Walk or Kayak the Calm Bayou Nature Park. The Casino has dance events and many eateries have live music. There are always art walks, vendors and markets throughout the month. This home has been recently renovated and all furnishings are brand new. It faces west for great sunset skies.

3

Bed

2

Bath

6

Sleeps

$127.69

/ Nightly

Private Vacation Home

Charming 2-bedroom bungalow with WiFi, AC in delightful Gulfport

Gulfport, Florida, United States

Discover the beauty of Gulfport from this 2-bedroom bungalow. Nestled in a serene neighborhood, this beautiful retreat offers 2 queen beds, a cozy living room with a sofa bed, and a relaxing bathtub in the bathroom. With amenities like AC, WiFi, and a washing machine, guests can enjoy a truly enjoyable stay. Experience the magic of Gulfport at our bungalow.

2

Bed

1

Bath

4

Sleeps

$248.76

/ Nightly

Private Vacation Home

Unique A-Frame Bungalow | Central Location

Gulfport, Florida, United States

Unique Gulfport Coastal Retreat — Perfect for Two Families, Couples, or Groups Seeking Privacy + TogethernessbrbrWelcome to this one-of-a-kind Key West–style A-frame bungalow, custom built by a world-renowned architect and perfectly located just one block from the water and a three-minute walk to Downtown Gulfport. Enjoy immediate access to the beach, fishing pier, restaurants, bars, local shops, and the vibrant waterfront district. A short walk the opposite direction brings you to the peaceful trails and wildlife of Clam Bayou Nature Preserve, and you're only minutes from both Downtown St. Petersburg and America’s top-rated beaches.brbrWhat makes this home truly special is its rare layout with two completely separate living areas, each with its own private entrance, kitchen, living room, bedroom, and bathroom. It’s an ideal setup for two families traveling together, two couples seeking privacy, or a larger family wanting a little extra space while still staying under one roof.brbrThe lower level features charming double barn-door entry, an open dining and living space with a cozy daybed, a fully equipped kitchenette, a large tiled bathroom, and a queen bedroom with private access to the lush backyard. The upper level showcases dramatic 20+ foot vaulted ceilings, a full kitchen, two small walk-in closets, in-unit laundry, a small office nook, and an outdoor deck with water views.brbrStep outside into your private tropical escape — a fully fenced yard filled with mango, avocado, banana, and citrus trees, plus an outdoor jacuzzi tub and shower surrounded by lush tropical greenery.brbrWith private parking, incredible walkability, and a flexible floor plan perfect for groups wanting privacy and comfort, this unique Gulfport home offers the ideal blend of charm, convenience, and coastal living for your next Florida getaway.

2

Bed

2

Bath

6

Sleeps

$198.31

/ Nightly

Private Vacation Home

A-Frame Canopy Suite Near Gulfport Beach

Gulfport, Florida, United States

Welcome to A Frame at Gulfport Gardens – Canopy Suite, a one-of-a-kind tropical retreat in the heart of Gulfport, Florida.brbrThis thoughtfully designed top-floor studio suite blends cozy comfort with unique architecture and an unbeatable location. Nestled on a quiet waterfront street surrounded by lush tropical landscaping and fruit trees, the property feels like a hidden jungle oasis while still being only a short walk from Downtown Gulfport.brbrPerched high in the tropical canopy, this one-of-a-kind bungalow offers a stay that feels closer to Bali or Costa Rica than a typical Florida rental.brThe space is cozy, elevated, and full of character — surrounded by lush greenery, mature palms, and a peaceful jungle-like setting. It’s intentionally more about atmosphere and experience than luxury finishes or oversized spaces.brbrThis is not a modern luxury resort or a large high-end condo. Instead, it’s a charming, tropical treehouse-style escape for guests who appreciate uniqueness, nature, and relaxed island energy.brIf your ideal stay includes personality, tropical ambiance, and morning coffee surrounded by palms and birdsong, this space may be exactly what you’re looking for.brbrInside, the suite features soaring vaulted ceilings, natural light, and a warm, inviting atmosphere perfect for relaxing after a beach day, biking adventure, or evening out in town. The space is designed to comfortably accommodate two guests with a queen bed, full kitchen, private bathroom, workspace, and everything needed for short or extended stays.brbrStep outside and experience the laid-back Gulfport lifestyle. Within minutes, you can walk to:br• Gulfport Beach and waterfrontbr• Gulfport Marinabr• Restaurants, bars, cafes, and local shopsbr• Volleyball courts and fishing pierbr• Clam Bayou Nature Preservebr• Pinellas Trail biking and walking pathsbrbrThe location is ideal for guests wanting both relaxation and convenience. Downtown St. Petersburg is only about 10 minutes away, while the Gulf beaches are approximately 8–15 minutes depending on which beach you visit. Tampa International Airport and St. Pete-Clearwater Airport are also easily accessible for longer stays and remote workers.brbrThe property itself is full of character, with tropical plants, mature fruit trees, water views, and a peaceful atmosphere rarely found this close to downtown amenities. Whether you're visiting for a weekend getaway, seasonal escape, remote work stay, or relocation transition, the Canopy Suite offers a comfortable and memorable home base.brbrPerfect for:br• Traveling professionalsbr• Snowbirdsbr• Couplesbr• Remote workersbr• Weekend getawaysbr• Mid-term furnished staysbr• Beach lovers and outdoor enthusiastsbrbrGuests enjoy private parking, a private entrance, and easy access to everything Gulfport and St. Petersburg have to offer.brbrCome experience the relaxed coastal energy, artistic charm, and tropical beauty that make Gulfport one of Florida’s hidden gems.

Bed

Bath

Sleeps

$232.72

/ Nightly

Private Vacation Home

Pet-Friendly Gulfport Home < 2 Mi to Beach

Gulfport, Florida, United States

Relaxation for the entire family awaits with a stay at this updated 4-bedroom, 2-bathroom vacation rental home nestled in Gulfport! Spend sun-soaked days on Gulfport Beach, catch a Tampa Bay Rays game at Tropicana Field, or peruse the boutiques and local eats in Downtown St. Petersburg, all located within a short drive. At sundown, retreat home to unwind on the back deck followed by a cozy movie night on the Smart TV around the wood-burning fireplace.brbr-- THE PROPERTY --brbrOutdoor Living w/ Private Yard | 6 Mi to Downtown St. Petersburgbr brBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Futon, Queen Murphy Bed | Additional Sleeping: Pack 'n Playbr brOUTDOOR LIVING: Furnished deck & patio, bistro lights, fenced yardbrINDOOR LIVING: Smart TVs, dining table, board games, wood-burning fireplace (starter set of wood provided), hardwood floorsbrKITCHEN: Stainless steel appliances, granite countertops, dishwasher, microwave, Keurig coffee maker, blender, toaster, dishware/flatware, breakfast bar w/ seatingbrGENERAL: Free WiFi, washer/dryer, linens/towels, A/C & heating, complimentary toiletries, ceiling fansbrFAQ: 5 exterior security cameras (facing out), stairs required for access, pets fee (paid pre-arrival)brPARKING: Driveway (2 vehicles), free street parkingbrbr-- THE LOCATION --brbrBEAUTIFUL BEACHES: Gulfport Beach Recreation Area (2 miles), Upham Beach Park (5 miles), St. Pete Beach (5 miles), Treasure Island Beach (6 miles), Fort DeSoto Beach Park (12 miles)brOUTDOORS: Bert & Walter Williams Pier (1 mile), Mariner's Cove Marina (1 mile), Clam Bayou Nature Park (1 mile), St. Pete Pier (6 miles), Hubbard's Marina (7 miles), Shell Key Preserve (10 miles)brAREA ACTIVITIES: Gulfport Casino (1 mile), Florida Orange Groves Winery (3 miles), Tropicana Field (4 miles), Imagine Glass Art Museum (4 miles), Dali Museum (6 miles), Museum of Fine Arts (6 miles), John's Pass Village (7 miles), Sunken Gardens (7 miles)brAIRPORTS: St. Pete–Clearwater International Airport (15 miles), Tampa International Airport (23 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $50 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to accessbr- NOTE: Your safety matters. This property features 5 exterior security cameras: 2 cameras are located on the front corners of the property facing the front yard/front entrance, 1 camera is on the back porch facing the back door entrance, 1 camera is in the backyard facing the backyard, and 1 camera is on the side yard facing the side walkway. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion. They will record when it first senses motion and 30 seconds after the last motion is detected

Bed

Bath

Sleeps

$172.55

/ Nightly

Private Vacation Home

Harbor Mist - Fresh & Friendly in Marina District Private Oasis

Gulfport, Florida, United States

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 guaranteed to make new friends. Or re-connect with your loved ones in the comfort of laid-back living spaces.brBright, 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 guaranteed to make new friends. Or re-connect with your loved ones in the comfort of laid-back living spaces.brbrSunshine-seekers are in for a real treat! Scenic walking trails are just a block-and-a-half away at the Clam Bayou Nature Park, sand and surf is just a mile from home, and a palm tree-lined outdoor oasis is yours to enjoy in absolute privacy. Gather for meals or margaritas at the shaded table, or settle into the hammock and let the sound of the fountain spilling over into the pond lull you to sleep.brbrWELCOME TO HARBOR MISTbrbrSun-dappled and freshly painted in ocean hues, the living spaces at Harbor Mist make you feel like you brought the beach home with you. There’s no stuffiness in the main living area—two cozy sofas in floral and palm tree patterns invite you to flop down and cool off in the A/C. Choose a flick on the flat-screen, grab a novel from the shelf, or fill your wine glass and settle in for chats in this chilled out space.brbrMornings are a special time at Harbor Mist - it’s when our guests come together to fill their bellies and plot the day’s adventures. Spread out your maps and guidebooks on the pass-through bar and pore through them with a warm cup of coffee in hand. Or flip pancakes and sizzle eggs in the recently renovated kitchen. With tons of prep space and white cabinetry with under-counter lighting, this space is well-loved by our guests. Dig in together in a cheerful dining area with leather chairs and accent lighting.brbrAiry and sweet, the two bedrooms (one queen-size, the other full) are restful retreats furnished with coastal accents and simple, soft linens. Unpack with ease into wall-mounted cabinets and private closets, and rinse off the sand in a tiled bathroom with shower and tub combination.brbrThe true show-stopper at Harbor Mist is the backyard. Lush, grassy, and oh-so-private, it’s like having your own palm-studded oasis just outside your door. Watch stars come out from the pond-side patio lounge space, snooze through lazy afternoons in the hammock, or bring dinner or a deck of cards to the shaded dining area. This is vacation, so take time to stop and smell the flowers—the yard is rife with tropical blooms.brbrTHE CHARMS OF GULFPORTbrbrLive like a local in the down-to-earth Marina District, where you can greet the day by shaking hands (and paws!) with residents on their morning strolls. Just a block-and-a-half from the marina and Clam Bayou Nature Park, relaxation here means serene nature walks and afternoons out on the water. Just over a mile away, Gulfport Beach offers a postcard-perfect setting for days in the sun, in the surf, on the volleyball court, or picnicking in the pavilion.brbrBut lazy days and sunshine aren’t all that Gulfport has to offer. This vibrant town is teeming with Key West charm and community spirit. From twice-monthly art walks to farmer’s markets, from 4th of July fireworks to Formula One boat races, there’s always something happening here. Just ask us - your instant local friends.brbrPets welcome with additional fee.Please do not bring dogs that are trained to protect you and to only respond to your commands.brbrExterior video cameras onsite.brbrReservations require the completion of a signed rental agreement including your credit card details. You are entering into an agreement with Splashy Ventures/Gulfport Florida and Splashy is the merchant of record for rent, taxes and fees.

2

Bed

1

Bath

5

Sleeps

$115.42

/ Nightly

Private Vacation Home

Lovely 2-bedroom bungalow in charming Gulfport

Gulfport, Florida, United States

Charming Bungalow in fabulous Gulfport. Completely updated 2023. Less than 2 miles to Gulfport downtown lifestyle, fishing pier & beach. 10 mins to St Pete Beach & 13 mins to downtown St Pete. Kitchen fully stocked for long stays, washer/dryer, dedicated dining room that can be used as office. Bedroom 1 has King bed and Bedroom 2 has a Queen bed. Both have a closet with hangers and a dresser to unpack. Extra pillows for different sleeping habits. Couch can sleep a 5th guest. It does not pull out into a bed. Recliner in living room. Wifi for guests and use your subscriptions to login to TV's. Both bedrooms have a TV. Bed sheets, pillow cases, bath towels and beach towels in home. 4 Beach chairs, one umbrella and a soft cooler. 1.8 mils walk to downtown Gulfport waterfront district. Gas grill & 3 bicycles available upon request. Beach gear in closet. TV's in living room & both bedrooms. Walk-in shower. Private patio. Owner is a Realtor & available if in market. 5th guest on couch.

Bed

Bath

Sleeps

$173.88

/ Nightly

Private Vacation Home

Tyn & Marty's Old-Fashioned Beach Cottage

Gulfport, Florida, United States

Clean, classic, uncluttered and one of the best locations in Gulfport! Retro original kitchen that has been tastefully updated. Walk to everything in Gulfport – shops, restaurants, parks and the beach Wood floors and comfortable bedrooms. A wonderful part of your vacation! 2 bicycles available with advance notice. The bathroom has a combo tub/shower. Large outdoor patio area with table, grill, and lounge chairs. The very large yard has a small fenced portion for a doggy relief area.brLaidback charm and the simplicity of life at the beach are what you’ll find at Tyn and Marty’s Beach Cottage, located in Gulfport’s Waterfront District. With 2 queen-size bedrooms, 1 bath, a deck overlooking its spacious yard, and an Old Florida vibe that feels like childhood summers, this is the perfect spot for disconnecting (and reconnecting). Never fear, though: there is WiFi! And Netflix! And central air!brbrTyn and Marty’s location is a big draw. Walk to shops, restaurants, dolphin-watching cruises, the library, golf, tennis courts, the fishing pier, and more. Walk just 5 minutes to the nearest beach. And watch the 4th of July fireworks from your front yard without stressing about parking. In fact, you never have to stress about parking here: 2 off-street parking spots are included.brbrAccessing the rental is easy, with a digital, keyless lock equipped with a unique code so you can arrive on your own time.brbrTyn and Marty’s welcomes non-aggressive dogs that are over a year old, and the fenced area in the yard and nearby dog park are big plusses for pet owners. Dogs do require our prior approval, though, so talk to us (Splashy Ventures) before you head down with your pup.brbrA CLASSIC GETAWAYbrbrWe like to say that Tyn and Marty's is your grandmother’s beach cottage. And for a lot of guests, that’s just what the doctor ordered.brbrClean, uncluttered, and, above all, welcoming, Tyn and Marty’s was most likely built in the 1920s and has aged very well; the original hardwood floors are in gorgeous condition.brbrThe two bedrooms - nicknamed “Seaside” and “Sand Dollar” - both have queen-size beds. Seaside also includes a TV for those who like to fall asleep to their favorite show. Note that Sand Dollar’s closet is home to the washer and dryer, which is great for packing light but does limit the amount of storage space available in that bedroom.brbrNewly installed mattress toppers add comfort to both beds. The shared bath - which is quite spacious for a 1920s home!—has been updated with new tile floors.brbrIf you have extra guests, we have an inflatable EZ bed that is available upon request. With these additions, Tyn & Marty’s sleeps 6 people (4 in beds).brbrGULFPORT AND THE WATERFRONT DISTRICTbrbrCyclists, joggers and strollers love being close to the Pinellas Trail, too. This 38-mile bicycle path runs from Tarpon Springs to St. Pete, passing through several quaint beach towns along the way.brbrGulfport itself is a beach town with a lot of heart. Weekly events in town - from concerts to art walks - keep your vacation calendar packed with activity. Or simply relax on the beach with “breaks” for delicious meals; Gulfport has a surprising number of mouthwatering restaurants for its size.brbrMore beaches await within an easy drive, including St. Pete Beach and Clearwater. Though you can walk a lot of places from Tyn and Marty's, and a car isn’t required, it is recommended that you bring one to best explore this vibrant area.brbrPets with additional fee. Exterior video camera onsite.brReservations require the completion of a signed rental agreement including your credit card details. You are entering into an agreement with Splashy Ventures/Gulfport Florida and Splashy is the merchant of record for rent, taxes and fees.

2

Bed

1

Bath

6

Sleeps

$371.28

/ Nightly

Private Vacation Home

St Petersburg / Downtown Gulfport Florida - Calypso House

Gulfport, Florida, United States

Our Calypso House is a newly renovated Two Bedroom / Two Bathroom Floridian Beach House. Stay in our 1947 historical beach house in the quaint coastal community of Gulfport / St Petersburg, Florida. brbrSpecifically, we are in the heart of Downtown Gulfport, a short walk to Gulfport Beach, Boca Ciega Fishing Pier, O Maddy’s and Pia’s Trattoria restaurants. It is a 15 minute drive to Downtown St Pete's and the Gulf Beaches.brbrTwo Bedroom / Two full-bathrooms and parking. Maximum 4-guests.

Bed

Bath

Sleeps

$99.63

/ Nightly

Private Vacation Home

Bindy’s Bungalow Your Secret Oasis

Gulfport, Florida, United States

**Discounts for stays 28 days or longer…Located only 2 blocks away from: the beach, downtown Gulfport, dog park, marina, city pier, volleyball courts, tennis courts, art shops, Casino, groceries. Enjoy a private screened porch. Let us know if you want to bring your dog (additional charge). Lounge on the patio.brbrWelcome to your spacious 1 bedroom apartment that has a new King size bed with a 10 Memory Foam mattress. There is a Twin size Pull out for a 3rd person or guest in the living room. Full bathroom with tub & newWater-Pic shower head. Large linen closet with bath & beach towels, linens, etc. Fully furnished kitchen with a stove & oven, microwave, 4 slice toaster, & a Keurig coffee maker. brbrEnjoy your breakfast on the private screened porch overlooking the mature tropical landscaping and large oak trees.brbrAir conditioning & heat. Hardwood & tile floors with area rugs. Dining room seats 3. Flat screen, smart TV in the living room with Netflix. Wifi available. Second floor; 1 flight up.brbrGuests will have access to a private entry. On the patio, there is a table & chairs and gas grille for guests & owner's use. Yard is fenced with gates. Fence is not suitable for dogs. Beach chairs & mats are located in the patio area.brbrOther things to notebrWe accept up to 2 mature dogs - but No Puppies. Dogs must be house broken, well mannered and be free of fleas. Pet fee is $15 per pet, per night. To book a pet or an additional person send us a request and we will send a special offer back. Our pricing includes Florida Sales & Tourist Taxes. brbrThe local restaurants are great. I mean it, they're great. There is a lot of variety and the prices are reasonable. But, if you want to cook at home, there are some equally great food stores, like Trader Joe's, The Fresh Market, Earth Origins, or everyone's favorite local grocer - Publix. No smoking on the property, inside or out including vaping. The distance to Boca Ciega Bay is 2 blocks. There is an area where you can go in the water with your dog, and another beach area for humans, only. brbrThis is a wonderful area for walking, whether you want to walk on the beach, along tree-lined streets, or in a park. A dog park is 2 blocks north of us and there are public tennis courts adjacent to it. The Gulfport Museum is adjacent to the tennis courts. Clam Bayou is 5-6 blocks east and you can walk the trails that include several boardwalks out into the mangroves. The other side of the Bayou is a municipal golf course. There are 4 public volleyball courts on the beach.

Bed

Bath

Sleeps

$275.75

/ Nightly

Private Vacation Home

Enjoy Coastal Comforts in our Stylish '60s Gulfport Home

Gulfport, Florida, United States

Come stay at our charming MidMod retreat in the heart of Gulfport, FL! Nestled along the Gulf Coast, our 3-bedroom home offers inviting living spaces and a serene outdoor patio in a quiet neighborhood. Just 10 minutes from pristine St. Pete beaches and a short walk to Beach Blvd., where you'll find boutiques, cafes, and restaurants. Explore local farmers markets on Tuesdays and enjoy exciting events nearby. Experience the perfect blend of small-town vibes and artistic flair in Gulfport!brbrWe will be available for you throughout the during your stay. Should you ever have any questions and/or concerns, please reach out to us directly through the platform you used to book your reservation. brbrGulfport, nestled along Florida's Gulf Coast, is a charming town blending small-town vibes with artistic flair. Its colorful downtown boasts boutiques and cafes, while galleries showcase local art. Nature lovers enjoy Clam Bayou Nature Park and Gulfport Beach. Culinary delights await at seafood joints and bistros. But what truly sets Gulfport apart is its tight-knit community, welcoming visitors with open arms to enjoy its relaxed atmosphere, vibrant arts scene, and stunning coastal views. It truly is a hidden gem just waiting to be discovered.brbrThis is a single-level family home, with 3 bedrooms and 2 bathrooms. There are no stairs. You'll have access to the entire home and fenced-in patio during your stay. There is space on the side of the home for 2 vehicles. Additional street parking is at your own risk. Laundry room is located in the home, detergent is provided. brbrKEY FEATURES:br✦ 3 bedrooms: primary with king bed, en suite bathroom; two others, one king, one queen, share retro-style bathroom.br✦ Smart TVs in each bedroom ensure personalized entertainment options for all guests.br✦ High-speed Wi-Fi throughout the property ensures seamless connectivity for work or leisure.br✦ Designated workspace, complete with desk monitor, and even a printer!br✦ ‘60s-style kitchen with classic features, stainless steel appliances, dishwasher, and all essentials for cooking.br✦ Complimentary coffee and tea are provided to kickstart your mornings or enjoy cozy evenings in.br✦ French doors lead to a peaceful outdoor patio with gas grill.br✦ Outdoor seating areas surrounded by lush greenery offer comfortable spots for you to relax and soak in the serene surroundings.br✦ In-unit laundry (washer and dryer), detergent provided. br✦ Linens, towels, and toiletries are provided, reducing the need to pack bulky items.br✦ Walking distance to trendy Coffee Shops, Restaurants and Stores in Gulfport Village. br✦ Only 10 minutes to the beaches! brbrHere’s a breakdown of the home so you know exactly what to expect!brbrWelcome to our beautiful MidMod Retreat, nestled in the picturesque town of Gulfport, FL. Built in 1963, this home has been lovingly preserved and thoughtfully enhanced to seamlessly blend modern amenities with the timeless charm of the '60s era.brbrAs you step inside, you'll discover polished Terrazzo floors that exude elegance, a kitchen recently remodeled to perfection, and abundant large windows that flood the space with natural light. With multiple inviting seating areas, this residence offers a warm and welcoming atmosphere, providing the ideal base for exploring Gulfport and its surrounding areas in style and comfort.brbr✿✿ BEDROOMS & BATHROOMS ✿✿brThere are a total of 3 bedrooms, each nestled on the right side of the home. The primary offers a comfortable king bed with two dressers and a large closet, as well as a private en suite bathroom with a walk-in shower and brand-new vanity. Down the hall, you'll find two more bedrooms, another king bed, and the other with a queen. Both of these bedrooms offer ample drawer and closet space to store all of your personal items, and they share a charmingly preserved pink retro bathroom with a shower/tub combo. All of the bedrooms are equipped with a smart TV for endless entertainment. brbr✿✿ KITCHEN & DINING ROOM ✿✿brThe 1960s-style kitchen offers many classic characteristics including a delightful blue color scheme, a rounded edge breakfast bar supported by funky rod iron A-frame legs, and a retro-style refrigerator to truly tie into the vintage vibe of the '60s. We've made sure to include all of the household kitchen items you'd expect to be able to cook up wonderful meals throughout your stay including pots/pans, a variety of crockery, a blender, various cooking utensils, a deep sink, and stainless steel appliances, including a dishwasher for easy clean-ups! brbrAdjacent to the kitchen sits a cozy dinette, accommodating up to six guests. French doors lead to a peaceful outdoor patio surrounded by lush greenery, complete with a gas grill and an additional dining table shaded by an umbrella, perfect for enjoying al fresco meals both day and night.brbr✿✿ LIVING ROOMS ✿✿brThis home boasts not one, but two inviting living rooms, each offering its own distinct atmosphere and purpose. The first, a refined yet cozy formal sitting room, provides the ideal setting to unwind after a day of exploration. Tucked away in one corner is a designated workspace, complete with a desk, monitor, and even a printer, offering the convenience of remote work whenever necessary.brbrThe second living space, a cozy den adjacent to the kitchen, serves as the heart of casual gatherings and family activities. Whether it's hosting board game nights, enjoying movie marathons, stealing a quick afternoon nap, or simply keeping an eye on the little ones while preparing meals, this versatile den offers a warm and welcoming environment for all.brbr✿✿ OUTSIDE ✿✿brStep into your own little hideaway nestled in the backyard, where the sweet sounds of birds chirping fill the air. With its lush greenery and hints of old Florida charm, this spot is perfect for unwinding after a long day. Kick back and relax on comfy lounge chairs, where you can soak up the sunshine or cool off under the shade of a convenient umbrella. Fire up the grill and rustle up something tasty to enjoy while you soak in the relaxed vibes. And for some friendly fun, gather around the Jenga blocks and let the games begin.brbr❂❂ We aim to provide a 5-star experience and can't wait to hear about your wonderful stay! ❂❂brbrWe suggest renting a car or utilizing ride shares like Uber/Lyft for your stay if you wish to discover areas outside of Gulfport Village. The beach is located 10 minutes away by drive. Beach Blvd. is located just a short 20 minute walk down the street. If you have questions or would like further directions or instructions don't hesitate to reach out! Would love to help. brbrTravel Times:brbrGulfport Village (Beach Blvd.) ⇄ 3 minutes brGulfport Beach ⇄ 6 minutes brGulfport Tuesday Fresh Market ⇄ 6 minutesbrSt.Pete Beach ⇄ 10 minutes brClam Bayou Nature Park ⇄ 8 minutesbrSt. Pete–Clearwater Int'l Airport ⇄ 30 minutesbrTampa Int'l Airport ⇄ 30 minutes brbrAdditional recommendations for local restaurants, shops, attractions and more can be found in our customized guidebook--which you'll receive upon booking!

Bed

Bath

Sleeps

$168.56

/ Nightly

Private Vacation Home

Cute & Cozy Cottage In The Heart of Gulfport

Gulfport, Florida, United States

Welcome to our Blueberry Gumdrop Cottage. Relax after a day at the beach or exploring the artsy and eclectic little piece of paradise that we love...Gulfport.brbrWalking distance to the Gulfport Marina and Boca Ciega Bay and a few blocks to Downtown Gulfport, with an array of restaurants and shops, you will enjoy taking in the sunset while having dinner, or as you walk along Williams Pier. Just 10 min to St. Pete Beach, (named one of USA's top beaches), and the Beautiful Gulf of Mexico. You can also explore the amazing Downtown St. Pete, just 10-12 min drive, with tons to see and do.

Bed

Bath

Sleeps

$147.36

/ Nightly

Private Vacation Home

The Sand Dollar - Historic Charm Meets Historic District Beach Chic

Gulfport, Florida, United States

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: preserved Shaker touches and cool coastal décor offer the ideal blend of laid-back beach vibes and old-school Florida elegance.brClassic 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.brbrWith a parlor-style living space and private, tropical patio, there’s no shortage of spaces to relax. And you’ll do so in style: preserved Shaker touches and cool coastal décor offer the ideal blend of laid-back beach vibes and old-school Florida elegance.brbrVenture out and find yourself at the center of a vibrant community, where you’ll fill your days with farmer’s markets or music festivals. Spend afternoons in the surf and evenings at diverse waterfront restaurants. It’s all here in Gulfport, a funky little community tucked within St. Pete.brbrA DAY AT THE SAND DOLLARbrbrWake up in a king-size bedroom with airy coastal accents to remind you that you’re on beach time. The en-suite master bath with a walk-in shower is great for refreshing for the day ahead or washing off the sand from your latest adventure.brbrSwing open the French doors to the living space, then grab a book or admire the treetop views from the cozy sofas. If you need a minute to check in with the real world, steal away to catch up on emails at the corner desk (free WiFi is also included).brbrAdditional guests can use the main en-suite bathroom and convenient half-bath off the downstairs laundry room. A queen-size EZ bed is also available if you’re bringing a crew of four.brbrSuited for prepping everything from beach picnics to gourmet cuisine, the kitchen is equipped with a full suite of appliances and all the pots, pans, and dishes you’d find at home.brbrShake a margarita and sip it in the upstairs sunroom, or prep feasts and share them in your private outdoor yard. This tropical-inspired space is draped by an enormous sail shade to keep afternoon gatherings cool—have a long lunch at the outdoor table, then recoup on the loungers or hammock.brbrWHY WE LOVE THE SAND DOLLARbrbrIts own hidden hangout in the midst of the Waterfront District, the Sand Dollar offers low-key relaxation to balance out Gulfport’s energy and excitement.brbrWe love its quaint charm as much as we love its proximity to fun and funky downtown, home to mouthwatering dining establishments, unique art galleries, and a full line-up of events. Visit during GeckoFest, a circus-inspired street event with chill tunes and can’t-miss costumes, or catch a bi-weekly ArtWalk.brbrFor some time in the great outdoors, take your four-legged family member on a stroll to the dog park, or peddle your way down the Pinellas Bike Trail. The Sand Dollar is just a short trip from Stetson School of Law and Eckerd College, making it ideal for families making a visit to campus.brbrFree Wifi. Neflix! Additional fee for pets. Aero bed available for 3rd or 4th person.brbrExterior video cameras onsite. The entrance is only through the alley and there are no views from the sunporch.Reservations require the completion of a signed rental agreement including your credit details. You are entering into an agreement with Splashy Ventures/Gulfport Florida and Splashy is the merchant of record for rent, taxes and fees.

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$290.91

/ Nightly

Private Vacation Home

Peach Hideaway - Caged, Heated Pool & Florida Room

Gulfport, Florida, United States

Peach is a 3 bedroom, 2 bathroom home with an enclosed screened pool (heated during the winter months) near the Gulfport entrance to the Pinellas Trail, Tomlinson Park and 1 mile from Gulfport Beach. Walk to the shops and restaurants in under 15 minutes. King sleep number bed in the master, Queen bed in the back bedroom near the pool. The third bedroom has a bunk, double and trundle bed combo perfect for kids or possibly 2 adults. The Florida room has a mini-split for additional cooling.brPeach Hideaway is a 3BR/2BA, pet-friendly beauty in Gulfport, featuring a heated swimming pool that’s a big hit with guests. brbrWalk to Gulfport’s beaches, restaurants, pier, and more, then come back to your bug-free pool with a screen enclosure. Nighttime lights and pool heating (76-78 degrees) from November through April mean the pool is always ready to welcome you (but not the mosquitoes!). brbrHANGOUTS GALOREbrbrPeach Hideaway’s quaint, cottage-chic exterior conceals a surprisingly spacious, open layout with plenty of room for your group of up to 8.brbrMix drinks and head to the pool and deck with a gas grill. Prep feasts in the roomy, remodeled kitchen (with dishwasher) then gather at the 6-8 person table in the large dining room. Bring a book to the Florida room/sunroom for a quiet afternoon read, or watch a movie on the flat-screen TV. Catch up in the living area, which has its own flat-screen and comfy furnishings. brbrThe Georgia couple who owns Peach Hideaway still vacations here with their daughter and her family, so you can count on a well-stocked, family-friendly experience. From pool/beach toys and kitchen gear to free Wi-Fi and Netflix streaming, they've thought of everything for seamless and relaxing beach getaways - with or without kids! brbrBED and BATH brbrThree bedrooms and two baths are all on one level (Peach Hideaway has no stairs). brbrThe first bedroom has a king-size Sleep Number bed.brbrThe second bedroom has a trundle/bunkbed setup that sleeps up to 4. The top bunk and tucked-away trundle both have twin-size mattresses; the middle bed is a full-size.brbrThe third bedroom features a queen-size bed and sliding door access to the pool and deck. brbrThe bathrooms are conveniently located at the front and back at the house, and neither is an en-suite. The larger of the two features a walk-in shower; the second has a tub/shower combination. A separate sink in the third bedroom makes morning and evening routines even easier. brbrGULFPORT AND BEYONDbrbrPeach Hideaway is is a 15-minute walk from the beach, downtown Gulfport's shops and restaurants, and from the pier. And there's always something happening in Gulfport, a self-proclaimed small town with a big heart. From the bi-weekly art walks and weekly farmers markets to yearly festivals celebrating the arts, the beach, and life in general, you'll find a cheerful, welcoming attitude in Gulfport that's downright addictive. You might not want to leave! brbrBut there is more to explore beyond Gulfport: Treasure Island, St. Pete and St. Pete Beach are equally beautiful, and all a quick 15-minute drive from Peach Hideaway.brbrRing video doorbell onsite. All appliances work great. Dishwasher May 2021. Dryer Jan 2022. Grill August 2022. Washing machine May 2024. The pool is caged (screened) but this will not keep out all wildlife. Spiders, snakes and geckos can and do get in. brbrReservations require the completion of a signed rental agreement including your credit card details. You are entering into an agreement with Splashy Ventures/Gulfport Florida and Splashy is the merchant of record for rent, taxes and fees.

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Sleeps

$133.98

/ Nightly

Private Vacation Home

Bungalow on the Boulevard! WiFi, AC, Walk to the Water, Restaurants, & Galleries

Gulfport, Florida, United States

Experience Gulfport like a local in this enchanting 1-bedroom bungalow in a 1936 Craftsman Duplex. Nestled in the heart of the city, our cozy retreat offers a wonderful escape for guests. Unwind in the comfortable queen bed after a day of exploring, or relax in the inviting living room with a plush sofa bed. Stay connected with WiFi, and enjoy the convenience of amenities like a relaxing screen porch, fully equipped kitchen, private laundry and Central AC. Immerse yourself in the magic of Gulfport at our charming bungalow.

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$576.3

/ Nightly

Private Vacation Home

The right location!!!

Gulfport, Florida, United States

This is a Five bedroom 3 bath home located walking distance to Gulfport Bay beach and pier and local rest and shops. This house has it all. Game room, pool table, ping pong table, to many games to count.

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$210.92

/ Nightly

Private Vacation Home

Coastal Beach House · Steps to Gulfport Beach

Gulfport, Florida, United States

The Beach House is a luxury retreat crafted to give guests a true Key West–style getaway. Ideally located just one block from Gulfport’s vibrant Main Street and a short four-block stroll to Gulfport Beach, this home offers the perfect blend of charm, convenience, and coastal living.brbrEnjoy a spacious 400 sq. ft. enclosed patio, a private backyard, a gas grill, and a cozy campfire pit everything you need to create unforgettable vacation memories.brbrGuests can look forward to a comfortable night’s sleep with a queen memory-foam mattress in the master bedroom and a hybrid memory-foam/coil mattress in the guest bedroom. Each bed is dressed with high-thread-count sheets, a plush down comforter, four medium-density pillows, cozy throw blankets, and bedside reading lights with convenient outlet and USB access. The master bedroom also features blackout blinds and a partial water view located just four blocks away.brbrThe Beach House accommodates up to six adults—two in each bedroom and two on the queen sleeper sofa. The sofa bed includes a 2` memory-foam topper and 550+ thread-count sheets to ensure a restful night.brbrAll guests are required to complete a registration process through our software after booking is confirmed. At any time, we may request government ID verification and a photo for the cardholder who placed the reservation. By submitting payment, guests agree to the Guest Rental Agreement posted on all booking platforms and our website.brThe kitchen is fully stocked with dishware, glassware, a 14-piece cookware set, baking pans, spices, a coffee maker, coffee, sugar, creamer, a blender, toaster, cooking utensils, and plenty of towels.brbrA washer, dryer, and detergent are provided for your convenience.brbrRelax in the spacious enclosed patio equipped with an oscillating fan, or grill your favorite meals in the private, dog-friendly, fully fenced backyard.brbrBeach towels are provided, and beach chairs and umbrellas are available for rent upon request.brbrFor added security, the property is equipped with 10 motion-sensor lights, 6 security cameras, and 4 microphones located at the exterior entry points. All check-ins are reviewed for guest safety.brbrTo ensure comfort, the home features central air conditioning and ceiling fans in every room. The entire home is supplied with purified water through a whole-house filtration system, softener, and descaler.brbrThe entire home, two card single file driveway, enclosed backyard, large side yard with a garden, and enclosed patio are all yours.brbrThe Beach House is a charming two-bedroom, one-bath home featuring a fully stocked kitchen—equipped with everything you need to prepare a full Thanksgiving dinner. Your dog will love the private, enclosed backyard, and you’ll appreciate the two-car driveway plus ample street parking in a well-lit, safe neighborhood.brbrFor larger groups, you can also rent the adjacent luxury unit, The Wine Cellar, a two-bedroom, one-bath home that accommodates up to six additional guests.brbrGulfport Beach is one of South St. Pete’s hidden gems. Enjoy soft white sand, professional volleyball courts, and peaceful intracoastal waters. From the bedroom window or the front of the home, you can catch a glimpse of the beach just down the street. Wood Ibis Park, located one block away, offers a scenic lake and walking paths. Gulfport’s Main Street filled with restaurants, shops, breweries, bars, and local market is only two blocks away in this quiet, safe neighborhood.brbrYou’ll be staying in the heart of the Gulfport community, within easy walking distance of everything:brbrGulfport Fresh Market – Every Tuesday morning, one block awaybrbrGulfport Art Walk – First Friday & Third Saturday monthlybrbrTwo local markets only a block awaybrbrEndless owner-operated breakfast, lunch, and dinner restaurantsbrbrCoffee shops, kava bars, vegan deli optionsbrbrUnique local boutiques and art shopsbrbrCommunity destinations: the library, senior center, recreation center, dog park, and the historic Gulfport Casino (dance hall)brbrSports amenities: basketball courts, volleyball courts, the pier, and the beachbrbrParks: Wood Ibis, Hoyt, Clymer, and Clam Bayou Nature ParkbrbrCity Marina, Gulfport Historical MuseumbrbrTwin Brooks Golf Course nearbybrbrAnnual events including GeckoFest, Gecko Art Show, Gecko Ball, and Beach Bums volleyball tournamentsbrbrDowntown St. Pete, just a 15-minute Uber ride, hosts First Friday each month with open-container walkingbrbrOnce you arrive, you can walk to nearly everything. Two markets are a block from the house, and the main Gulfport strip is close by perfectly convenient for enjoying all the local charm.brbrFEES & IMPORTANT INFORMATIONbrbrOne-time Administrative Fee: $50 per reservationbrbrPet Policy: “Pet Fee” applies to dogs only. Any other animals must be approved by management and may incur up to a $700 fee.brbrbrLocal OrdinancesbrGulfport allows a limited number of 30-day minimum stays. Contact Beggins Luxury Vacation Rentals for seasonal rental details.brbrSleeping ArrangementsbrThe Beach House accommodates up to 6 guestsbrbr4 guests in two queen bedsbrbr2 guests on a queen sleeper sofa with a 2` memory-foam topper

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$215.88

/ Nightly

Private Vacation Home

Gulfport Retreat with Wine Cellar Charm

Gulfport, Florida, United States

The Beach Wine Cellar is a two-bedroom one-bathroom luxury home designed to immerse the guest in a Tuscany style vacation on the beach. Conveniently located 1 block from main street and 4 blocks from Gulfport Beach. Boasting a bar for 2, a living room for 6 with a 55` TV, an indoor dinning-room. There is an enclosed backyard with a privacy fence. The patio has a barbecue and a gas fire-pit. Enclosed 450 SF patio has 4 fans, dinning table, a living room set, 55` TV, and games.brbrGuests can look forward to a restful night’s sleep with a queen memory-foam bed in the master bedroom and a hybrid memory-foam/coil mattress in the guest bedroom. Each bed features high-thread-count sheets, a luxurious down comforter, four medium-density pillows, cozy throw blankets, bedside reading lights, and convenient access to three outlets and two USB ports. The master bedroom also offers a partial water view and blackout blinds for optimal rest.brbrThe Wine Cellar comfortably accommodates up to six adults two in each bedroom and two on the queen sleeper sofa, which includes a 2` memory-foam topper and 500+ thread-count sheets to ensure a great night’s sleep.brbrThe kitchen is fully stocked and ready for use, complete with dishware, glasses, a 14-piece cookware set, baking pans, spices, a coffee maker, coffee, sugar, creamer, a blender, toaster, ample towels, and all essential cooking utensils.brbrA washer and dryer are available for your use, with detergent provided.brbrRelax in the spacious enclosed patio, equipped with an oscillating fan, and enjoy grilling meals on your private barbecue. The fully fenced backyard is dog-friendly, offering comfort and convenience for you and your pets.brbrBeach towels are provided for your trips to the shore, and beach chairs and umbrellas are available for rent upon request.brbrFor guest safety, the property is equipped with 10 motion-sensor lights, 5 security cameras, and 4 microphones located at the entryways. All check-ins are monitored for security purposes.brbrTo ensure comfort, the home features central air conditioning and ceiling fans in every room. The thermostat is preset between 70° and 80°; please contact your host if you need a temperature adjustment. The home’s water supply runs through a whole-house filtration system and descaler for cleaner, fresher water.brbrThe Wine Cellar is a two-bedroom one-bath with a full kitchen. You can enjoy the outdoors with the propane fire pit provided or sit back in the large enclosed patio enjoying the game room. Your dog will enjoy a private enclosed yard just for them. The Wine Cellar has a four-car driveway and plenty of street parking in a well-lit safe area. The driveway is big enough to fit an RV, Boat, or trailer but there are additional fees for such parking.brbrLocal ordinances allow a limited number of 30-day minimum stays. Please call Beggins Luxury Vacation Rentals for further questions regarding your seasonal rental.

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$278.46

/ Nightly

Private Vacation Home

Gulfport Putting Green Fire Pit 2/2

Gulfport, Florida, United States

Welcome to your vibrant coastal retreat nestled in the heart of artsy, laid-back Gulfport! This thoughtfully designed 2-bedroom, 2-bath home combines classic Florida charm with modern comfort — perfect for families, couples, or small groups seeking relaxation and fun.brbrStep inside to a bright Florida sitting room, where morning sunshine pours through large windows, creating the perfect spot for coffee or a quiet read before the day begins. The inviting living room offers cozy seating for unwinding after exploring nearby beaches or Gulfport’s lively waterfront district.brbrThe dining room seats four comfortably for meals or card games, while the fully equipped kitchen features a breakfast bar for two — ideal for sipping mimosas or chatting with the chef. A washer and dryer are tucked conveniently in the adjoining laundry area for longer stays.brbrThe king master suite includes a private en-suite bathroom, while the second bedroom features a plush queen bed with easy access to the guest bath, offering everyone a peaceful retreat after a day in the sun.brbrStep outside to your private backyard escape — a true highlight of this property! Enjoy a friendly competition on the putting green, then gather around the fire pit beneath the stars. The outdoor dining area for six and grill make it easy to cook up a beach-style barbecue and enjoy Florida evenings in style.brbrLocated just minutes from Gulfport Beach, the pier, and the eclectic shops and cafes of Beach Boulevard, this home captures the spirit of Old Florida with the comforts of today.

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$156.63

/ Nightly

Private Vacation Home

Old Florida Cottage in a Private Gulfport Oasis

Gulfport, Florida, United States

Nestled into a private oasis of palm trees and flowers, The Montgomery Cottage in Gulfport offers guests a comfortable stay in this unique Old Florida neighborhood. The property itself is lushly landscaped with seasonal flowers, lemon and lime trees, plantains, Ice Cream bananas, mangos, loquats and more. If the fruit is ripe, help yourself. Nothing beats eating fresh fruit from the tree. The landscape is a photographer's muse and the back porch is perfect for relaxing with a coffee, cocktail or reading one of the many books from the house library.brbrInside you will find two comfortable bedrooms, one with a queen bed, the other a full size, fully dressed with fresh linens. There is a bathroom with bathtub and shower wand, stocked with beach and bath towels, soap and shampoo. The kitchen has enough coffee to get you started, is fully equipped to prepare a meal and offers a beautiful view through large bay windows.brbrThere are two rooms for lounging, reading or watching tv. One is the library room stacked with hundreds of books, a leather couch and recliner, and flatscreen smart tv. The other has porch access, an additional leather couch and a tv/dvd player with a collection of over 300 DVD's for the rare rainy day. There is a laundry room with washer and dryer for your convenience.brbrGuests have access to the outdoor storage shed for use of beach chairs and toys, golf clubs, coolers, tennis rackets and basketball for the community course, courts and beaches.brbrYou will find the Montgomery Cottage is ideally located to explore all that Tampa Bay has to offer with quick access to the interstate and 2 major airports, yet close enough to explore the community on foot. brbrEclectic downtown Gulfport is a 15 minute walk through the Art District and past historic homes and parks. Gulfport Beach and Clam Bayou Nature Park is 5 minutes further. brbrTwin Brooks Golf Course and Stetson Law School is a 5 minute drive. brbrThe property is only a 12 minute drive from award winning St Pete Beach and the same distance to the museums, shopping and nightlife of vibrant downtown St. Petersburg. brbrNationally acclaimed Fort Desoto State Park is a scenic 20 minute drive. brbrWhether you stay with us for a few days, a week, a month or more, we're sure you'll enjoy yourself here in Gulfport. We love it here at the Montgomery Cottage and believe you will too.brbr*Please note: It's possible you may meet Judge, a beautiful and friendly outdoor cat who spends time lounging in the garden shade. Treats are available if you want to make friends.brAs we've created an oasis in the center of it all, you may see a raccoon walking around at night or a possum loaded with baby joeys waddle through the yard. Please be kind. Our neighbors are artists and critters too.

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