Family-friendly holiday rentals in Gulfport

The living room features a striped sofa adorned with decorative cushions displaying tropical patterns. A glass coffee table sits at its center, complemented by wooden side tables. Large windows draped with patterned curtains allow natural light to enter, illuminating the space.

4.92 out of 5 average rating, 104 reviews

Salty Air Retreat 10 minutes to St Pete Beach

This newly remodeled "Old Florida" boutique home has plenty of room to enjoy with family or friends. We offer 2 bedrooms, a large family room with sleeper sofa, living room, large open concept kitchen, fenced in yard with tiki bar and lots of outdoor seating. Set in a peaceful neighborhood only 1 mile to Gulfport, 5 miles to DT St Pete and 3.5 to SP beach, with some of Tampa Bay's best attractions close by, you can't go wrong with the location. Ample driveway and street parking. Self checkin

Indoor spacesKitchenSleep quality

A spacious backyard is featured, bordered by a wooden fence for privacy and lined with tropical plants and trees. A concrete patio area is included, which features a grill covered for protection. The lawn is open and well-maintained, providing a serene outdoor space.

4.97 out of 5 average rating, 179 reviews

The Pelicans Roost / Gulfport

The Pelicans Roost is a remodeled home, with a new fully stocked kitchen with all your cooking and entertaining needs. All new furnishings, a screened in back porch and a patio with an outside table and grill. The yard is completely fenced and lined with tropical plants and trees for your privacy. This spacious and comfortable home is clean and in a quiet neighborhood just 5 blocks from all that downtown Gulfport has to offer- the Marina,Beach,Restaurants, Shops, Fishing, Galleries and more...!

Indoor spacesFamilyQuiet

An aerial view captures a coastal neighborhood with colorful homes, palm trees, and a serene waterfront. A pier extends into the water, and boats are anchored nearby, surrounded by lush greenery. The vibrant blue sky contrasts with the calm sea, creating a tranquil atmosphere.

4.86 out of 5 average rating, 105 reviews

Blue House

This Home was NOT affected by by the Hurricanes! Gulfport waterfront sustained significant damage. So please check with the local municipality for any updates on recovery status of areas affected. Walk to everything, 5 ensuite bedrooms, NEW Vacation home in Gulfport. - Kitchen is fully stocked with a coffee maker, blender, toaster, mixer, pots & pans, dishes, and cutlery. - Free parking for 4 vehicles - Professionally Cleaned and Sanitized - 5 bedrooms w/ queen size beds, private bathrooms,

KitchenFamilyTV

4.91 out of 5 average rating, 275 reviews

A private yard is showcased with a spacious patio featuring a picnic table and four chairs arranged around a firepit. Lush green grass surrounds a stone pathway, and a large umbrella offers shade. The home’s blue exterior is visible in the background.

Tiny home in Gulfport

Pelican's Nest - Tiny House

The Pelican’s Nest is a cozy tiny home designed with your comfort in mind. Enjoy relaxed, beachy vibes inside, or unwind in your private yard perfect for connecting with nature, dining outdoors, or gathering around the fire. Traveling with a pet? They’re more than welcome here. Located just one mile from Gulfport’s Beach Blvd, you’re close to local shops, restaurants, and waterfront strolls. And only six miles away, you can explore St. Pete Beach or spend the day at the iconic St. Pete Pier.

Indoor spacesFamilyNearby

4.95 out of 5 average rating, 247 reviews

A charming pool area is surrounded by lush tropical foliage. The turquoise saltwater pool is framed with light stone paving. A small cottage with a red door is visible in the background, while lounge chairs and a colorful beach ball provide inviting accents to the outdoor space.

Guesthouse in Gulfport

A slice of paradise!

The guest cottage (approx. 300 sq ft) is separate from the main house, where we reside, with a beautiful saltwater pool to cool off in after your day's adventures! The property is 5 blocks from downtown Gulfport, with waterfront restaurants, bars, arts district, unique shopping, and beach. Close access to new tennis courts, bayside beach and minutes away from modern downtown St. Petersburg, and world-famous beaches. We are not set up to host pets or children and no unaccounted for guests.

Indoor spacesKitchenSleep quality

4.95 out of 5 average rating, 170 reviews

A heated stock tank pool is surrounded by a lush tropical landscape featuring a variety of green plants. An oversized umbrella provides shade, and a colorful bungalow is visible in the background, creating a serene outdoor retreat.

Tiny home in Gulfport

Shipwreck Bungalow

Shipwreck Bungalow, your own private paradise! Nestled in a quaint Gulfport neighborhood. Just 10 minutes from St. Pete beach, 10 minutes from lively downtown St. Pete and a few short minutes from funky downtown Gulfport. The Bungalow is surrounded by palms, tropical plants and flowers, beautiful outdoor shower, Tiki bar, heated stock tank pool, fire pit, outdoor games, grill and spacious outdoor seating area. Enjoy lounging by the pool or exploring all this sunny area has to offer!

KitchenIndoor spacesNearby

4.98 out of 5 average rating, 125 reviews

Cozy Cottage for Lovers

Relax, reconnect and revitalize in this private, intimate cottage that has everything you need to leave the hustle and bustle behind. Surrounded by lush tropical vegetation in the shade of giant live oaks and located in the Gulfport Arts District, you're a short walk or bike ride from excellent urban parks, restaurants, live music, fashion and art boutiques, dancing at the Gulfport Casino, community theater, and a beautiful beach that looks out over sailboats moored in Boca Ciega Bay.

Indoor spacesKitchenGetting around

4.94 out of 5 average rating, 143 reviews

An inviting view into the living area is framed by a decorative arch. A vibrant green plant adds a touch of nature, while a cozy brown couch and accent chairs are arranged around a circular coffee table. Colorful artwork decorates the walls.

Guesthouse in Gulfport

Gulf Guesthouse - king bed, 3 blocks to downtown.

Be our guest! Welcome to our family compound where you will enjoy the treetop views from our second story carriage house guest apartment. You'll be surrounded by the tropical serenity of lush palms and plants, both inside and out, while being just around the corner from the excitement of downtown Gulfport. Our updated one bedroom apartment is fully furnished and stocked with all of the things you'll need for an extra comfortable, enjoyable stay. We look forward to hosting you!

FamilyKitchenComfort

4.93 out of 5 average rating, 138 reviews

An outdoor patio area features a tiled surface surrounded by greenery and a wooden fence. A round table with chairs is positioned next to a gas grill, while a large tree provides shade. Potted plants add a touch of nature to the space.

Tiny home in Gulfport

Avocado Casita 10 mins to Beaches

Newly built studio -- small space, smart design. An intimate studio space meant for a minimalist lifestyle complete with full amenities. Compact yet comfortable, it’s the perfect place for a restful sleep in between your daytime adventures. Pack light, live easy. 3 blocks from Stetson Law School 3-4 blocks from the Pinellas Trail ~1.5 miles to Gulfport’s Beach Blvd 3 miles to Award Winning St. Pete Beach 4 miles to Award Winning Treasure Island ~4.5 miles to Downtown St Pete

KitchenFamilyCondition

4.99 out of 5 average rating, 289 reviews

Gulfport Art District - One Block From Beach!

Welcome to Uncle Finley's! Situated in the heart of Gulfport's Art and Waterfront District, This cottage listing is for unit A of the duplex. Step outside and walk to Gulfport Beach only one short block away, experience the highly-rated restaurants and shops, or browse local arts and crafts during the weekly Tuesday Morning Market during your stay. Want to experience more of Tampa Bay? Downtown St. Pete, St. Pete Beach, and I-275 access are only ten minutes away.

Indoor spacesKitchenWi-Fi

The exterior of the duplex is showcased with a brick facade and a light blue roof. A small white door is centered under a decorative wall feature. Potted plants and a small bistro table with chairs sit on a grassy area, surrounded by trees.

5.0 out of 5 average rating, 145 reviews

Peaceful Getaway Close to Amazing Beaches!

This property is nestled in a quiet neighborhood just a mile from the beautiful Gulfport Waterfront District. It’s the perfect place to get away and relax or work remotely! You’ll be in the front unit of a duplex, minutes away from our awesome town of Gulfport, renowned beaches on the Gulf, gorgeous local parks and preserves, lots of artsy shopping spots, and dining options for every palette! This sanctuary is furnished with everything you might need!

KitchenIndoor spacesCleanliness

Two light blue beach cruiser bicycles with tan seats are positioned on a concrete surface. A window and a chair in a welcoming yellow tone are visible in the background, framed by greenery. The entrance to the rental is accessible and inviting.

4.85 out of 5 average rating, 189 reviews

Gulfport Getaway-Close to Everything!

Take a step off the beaten path with a stay at this tropical 2-bedroom, 1-bath Gulfport Beach vacation rental! The 'Sirens Cove' is ideally situated between St Pete Beach, downtown St. Petersburg, and the quirky, vibrant Gulfport Arts District. Take a ride on our beach cruisers and enjoy the Gulfport vibe! You'll have plenty of opportunities to recharge your soul, relax, and soak up the beautiful Florida sun! 30+ Day Rentals Available!

Indoor spacesFamilyBiking

Popular amenities for Gulfport family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A sunlit sunroom features a wooden dining table surrounded by six woven chairs. A tropical-themed mural adorns the wall, depicting surfboards and palm leaves. Large windows and sliding glass doors offer views of the outdoor space, while a vibrant rug adds a pop of color to the floor.

4.9 out of 5 average rating, 110 reviews

Heated Pool~2 Miles St Pete Beach~Hot Tub~Games!

KitchenFamilyGetting around

4.71 out of 5 average rating, 117 reviews

Waterfront Oasis, Hot Tub, Sauna

Indoor spacesFamilyTV

4.96 out of 5 average rating, 115 reviews

A view from the balcony showcases a sandy beach lined with palm trees and manicured green lawns. The calm blue water reflects clear skies, while a distant shoreline is visible. A bench can be seen on the grass, inviting relaxation.

Condo in Isla del Sol

Isla Sunsets

KitchenFamilyLong stay

4.92 out of 5 average rating, 150 reviews

A comfortable living area features light-colored furnishings with striped patterns, complemented by a large artwork on the wall. A round coffee table sits in the center, while a ceiling fan provides airflow. Floor-to-ceiling glass doors offer a view of the Gulf and access to a balcony.

Condo in St. Pete Beach

1145 Sqft! - 2 Bedroom 2 Bath (GULF FACING!) Condo

FamilyKitchenCleanliness

4.89 out of 5 average rating, 112 reviews

Condo in Tierra Verde

Island Escape • Pool • Jacuzzi • Minutes to Beach!

FamilyIndoor spacesHospitality

Guesthouse in St. Petersburg

Private Guesthouse in St. Pete w/ Pool & Jacuzzi

KitchenIndoor spacesBackyard

4.86 out of 5 average rating, 147 reviews

A modern living room features a stone accent wall with a large flat-screen TV mounted above a contemporary electric fireplace. Comfortably arranged seating includes a gray sofa and an accent chair. Natural light filters through the window, illuminating the space.

4.86 out of 5 average rating, 226 reviews

Tropical escape house with hot tub

FamilyIndoor spacesHospitality

A screened-in outdoor area features a heated swimming pool, surrounded by paver stones. Two lounge chairs are positioned nearby, and colorful floaties are visible in the water. The scene is framed by trees and a lawn in the background, with sunlight filtering through.

4.92 out of 5 average rating, 198 reviews

Heated Pool and hot tub luxury vacation house

FamilyKitchenCleanliness

Family- and pet-friendly home rentals

A welcoming living area features light-colored seating with orange and gray accents. A wooden coffee table is centered on a decorative rug. Natural light filters through the vertical blinds, illuminating the room's neutral tones, complemented by a potted plant and wall-mounted lighting.

4.91 out of 5 average rating, 191 reviews

Hibernate in our Bear Creek Home

Indoor spacesKitchenLaundry

4.88 out of 5 average rating, 144 reviews

A spacious bedroom features a king-size bed with a blue quilt and accent pillows, complemented by bedside tables with lamps. A small dining table sits in one corner, with artwork displayed on the wall and natural light coming from a nearby door.

Apartment in Gulfport

The Peaceful Turtle Retreat

Indoor spacesFamilyCleanliness

4.85 out of 5 average rating, 99 reviews

Fresh & Friendly in Marina District Private Oasis

Indoor spacesFamilyCheck-in

4.76 out of 5 average rating, 218 reviews

A spacious saltwater pool stretches across the backyard, bordered by a paved area featuring lounge chairs. Lush greenery, including palm trees and a nearby canal, enhances the serene outdoor setting under a clear blue sky.

Villa in St. Petersburg

Dolphin Cove Waterfront St. Pete Beach w/ Pool

KitchenIndoor spacesAccuracy

Guest suite in St. Petersburg

The inviting guest suite showcases an open living area with a wooden floor and natural light. A round dining table and chairs sit next to a cozy armchair. A kitchenette is visible in the background, with a small bar and various amenities. Walls are adorned with artwork.

Central Oak Pet Friendly Retreat

KitchenIndoor spacesLocation

4.94 out of 5 average rating, 216 reviews

Guest suite in St. Petersburg

A private garden space is presented, featuring a small wooden table with two folding chairs positioned on a red pathway. Lush greenery, including a palm tree and flowering plants, surrounds the area, creating a serene outdoor setting.

Charming Side Garden Suite (no cleaning fee)

Indoor spacesKitchenEV charging

4.95 out of 5 average rating, 194 reviews

4.98 out of 5 average rating, 193 reviews

Home in Pinellas Park

Insta Worthy Retreat -HTD Pool- Arcade Room- Golf

KitchenIndoor spacesCondition

5.0 out of 5 average rating, 23 reviews

Guest suite in Gulfport

Private Yard - Gulfport

Indoor spacesFamilyWalkability

Family-friendly home rentals with a pool

A screened-in saltwater pool area is highlighted, featuring colorful pool floats and two blue lounge chairs. Natural light enters through large windows, and a door provides access to the adjacent living space. The bright walls reflect the sun, enhancing the cheerful atmosphere.

4.94 out of 5 average rating, 161 reviews

Creamsicle Dreamsicle- Saltwater Pool- Near Beach!

KitchenFamilyAccuracy

4.87 out of 5 average rating, 135 reviews

Inground Pool w/ Game Room - Fully Renovated House

Indoor spacesKitchenBarbecue

Guest suite in St. Petersburg

The living area features a comfortable seating arrangement with a patterned armchair and a dark leather couch. A wooden coffee table is positioned atop a large area rug, while natural light filters through sheer curtains, illuminating the space. A small dining table is set near the entrance.

Suite Retreat in Southwest St. Petersburg

Indoor spacesKitchenHospitality

4.99 out of 5 average rating, 182 reviews

4.98 out of 5 average rating, 102 reviews

Pet Friendly Pool Oasis St Pete/Gulfport

Indoor spacesFamilyWalkability

4.95 out of 5 average rating, 159 reviews

An outdoor patio area features a dining table adjacent to a heated pool. Lounge chairs are positioned nearby, under a screen enclosure. The pool is framed by a laid stone surface, with a view of lush greenery beyond the surrounding fence.

Villa in St. Petersburg

Heated Pool! Huge Walk In Shower! 5 min to beach!

FamilyIndoor spacesSleep quality

4.96 out of 5 average rating, 184 reviews

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

Indoor spacesKitchenBeach

4.99 out of 5 average rating, 231 reviews

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

Condo in Treasure Island

Spectacular beach to bay views from this resort.

Indoor spacesKitchenBathroom