Family-friendly holiday rentals in Upham Beach Park

A bright living area features a sofa and two leather armchairs beside a dining table with four chairs. Light-colored walls and ceiling tiles create an open atmosphere, while coastal artwork adds a touch of color. A plush area rug enhances the space.

4.96 out of 5 average rating, 178 reviews

Beautifully upgraded condo steps to the sand!

Relax in this beautifully remodeled 1 bed 1 bath condo located steps away from the white sands of Upham Beach! Several restaurants & beach bars within walking distance- no need for a rental car if you don't want one. Full kitchen includes a Keurig and all essentials for cooking including pots, pans, blender, ect. Closet includes all you need for a great day at the beach: towels, chairs, umbrella, cooler, and a wagon to transport it all with ease or enjoy the pool! Pack & Play included for kids.

A private entrance is visible, highlighted by a bright blue door adorned with a sun-shaped decor. Lush greenery and vibrant flowers frame the pathway, leading to a serene courtyard featuring lounge chairs, enhancing the inviting and tropical ambiance.

4.91 out of 5 average rating, 164 reviews

Tropical Courtyard Paradise on St. Pete Beach

Charming, cozy, well-appointed/fully stocked ground floor 1 Bedroom Unit with its own Private Entrance, Courtyard & spacious heated Pool. A short 1 minute walk to either St. Pete's Gulf side Upham Beach or all the abundant Nightlife & Restaurants on Gulf Blvd. Free WiFi(Spectrum) & 2 separate 32" HD TV's (Living Room sofa bed & Bedroom Queen bed), have all premium, movie, news, & sports channels. This Unit is affordably priced for the Budget Conscious desiring that Premium Beach Location.

Guest house in St. Petersburg

A private backyard features a heated pool surrounded by lush tropical plants and trees. The pool has a gentle curve and is accompanied by stone steps leading into the water. A small seating area is partially visible in the background, set amongst vibrant greenery.

4.98 out of 5 average rating, 221 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

Welcome to cute & cozy Turtle Cottage located right in the center of St. Pete, close to both Downtown AND several gorgeous Florida beaches. NO CLEANING FEE with competitive, seasonal pricing = a FANTASTIC DEAL for this space! A BEAUTIFUL NEW HEATED POOL & HOT TUB await in the private, fenced-in tropical backyard. Sorry, no pets/animals or babies/children/teens. Adults 21+ only and limited to 2 verified guests. 100% smoke-free property, inside & out. EVERYONE is welcome here. Come & enjoy!

Guest suite in St. Petersburg

A comfortable sleeping area features a queen bed dressed in a white and aqua patterned duvet. Two individual pillows rest at the head of the bed. A nightstand with a lamp and a decorative chair are positioned nearby, while light from windows partially covered by blinds illuminates the space.

4.98 out of 5 average rating, 971 reviews

Private Guest Suite 2 miles from Beach

Private, small completely renovated Guest Suite with Private parking, private separate entrance with deck. Space is best for 1-2 people: small, but thought out. 2 miles from Treasure Island beach. 2.5 miles from the St Pete beach! Beautiful quaint neighborhood. Near great fishing spot Kitchenette Full Bathroom Comfy queen size bed Cool AC unit ❗️WE HAVE GREAT REVIEWS, but please view before booking “Is this guest suite right for you” below under “things to note” to have the trip you desire

Guest house in St. Petersburg

The exterior of a cozy converted workshop features a gray wood-paneled facade with a vibrant yellow front door. Two chairs are positioned on the porch, beside a barrel and trash bins. A privacy fence can be seen in the background, surrounded by greenery.

4.84 out of 5 average rating, 869 reviews

Private & Cozy Tiny Home/Cottage

This is a cozy converted workshop with all the amenities of a traditional home! You'll have a comfy bed that sleeps 2 with an air mattress upon request, TV with streaming options, fun decorations, WiFi, air conditioning, W/D, closet space, cooking stuff, & bathroom. If you love tiny homes, you'll love this. Because of it being a converted workshop, it still has that feeling in some regard. It's a little rustic, but still charming. It's not a hotel, nor does it try to be. Pets are welcome.

A scenic view of a heated pool is highlighted, with sun loungers positioned under yellow umbrellas along a sandy beach in the distance. A cozy living area features a comfortable couch and a dining table, while a second image showcases the inviting pool area with surrounding greenery.

4.9 out of 5 average rating, 217 reviews

Quiet condo with heated pool- 4min walk to beach!

Experience the ultimate beachside getaway in our cozy 1st floor unit in a gated condo. Great choice for those wanting to relax like a Floridian with a pool and the beach just steps away. Enjoy this quiet section of Upham beach for your perfect vacation! Our condo comfortably accommodates up to 5 guests with a king bed, a memory foam sofa bed, and an air mattress. Washer and dryer, plus parking for 2 cars. Blocks away you’ll find dozens of restaurants, as well as grocery stores and shopping.

4.91 out of 5 average rating, 170 reviews

Family Friendly Condo

Cute beach condo within seconds of walking you are on the beach! The Gulf Winds Resort community is quiet and clean! One of the quieter areas of St. Pete Beach, but within walking distance to a bunch of fun restaurants and bars! There is a pool and shuffle board on the resort property and charcoal grills. One of the best views of the sunset at the beach! *please note this is a 2nd floor unit, no elevator*this resort is a family friendly resort and follows STRICT rules of noise ordinances*

4.96 out of 5 average rating, 129 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!

4.8 out of 5 average rating, 152 reviews

A view from the window captures a tranquil scene of the beach, with sandy shores and beach umbrellas in the distance. Palm trees frame the image, alongside a glimpse of an adjacent street and a nearby pink building. An American flag gently waves in the breeze.

Flat in St. Pete Beach

St Pete Beach Home - Gulf views & great location

Enjoy beautiful sunsets & beach views from the private deck. This 3rd floor condo is steps from the beach. The main BR has a new king bed, flat screen (Cable) plus access to the private deck. The second BR has a new queen bed, flat screen (Roku) plus ocean views. The living area has a sleeper sofa, recliner, & flat screen (Cable). The kitchen has new appliances & granite counters. The condo has dedicated high speed internet. The location is fabulous! CONSTRUCTION ON PROPERTY

A condominium complex is shown, featuring a colorful sign that reads 'The Friendly Native' amidst well-maintained landscaping. Palm trees and bushes with vibrant flowers are visible in the foreground, while the two-story buildings display balconies and large windows.

4.85 out of 5 average rating, 183 reviews

🏝 St Pete Beach Condo🏝

Walk right out to the white powdery sand and crystal blue water of the Gulf of Mexico from this ground-floor luxury unit. Spacious 1BR/1BA condo, fully furnished, beautifully decorated, and equipped for vacation rentals. Tropical courtyard with heated pool, grill & lounge. Step through the gate—you're on St. Pete Beach. Breathtaking sunsets included. No pets. No smoking. Book your stay now and experience the magic of beachfront living—paradise awaits you every single day.

A bright living area features a comfortable gray sofa adorned with striped pillows. Natural light highlights a wooden coffee table, positioned between two woven ottomans. A serene wall art piece and a lamp provide ambient lighting, while a decorated entrance door is visible in the background.

4.85 out of 5 average rating, 195 reviews

Sunset Condo: Steps to the Beach with Pool Access

Relax in this updated condo just steps from the beach in St. Pete Beach! This family friendly second floor unit has one bedroom with two full beds, a bright living area, an updated bathroom, and a full kitchen. Catch views of the Gulf of Mexico from the private balcony! Location is everything and Sunset Condo is steps from the beach and its amazing sunsets, and within walking distance to waterfront restaurants with live music, coffee shops, & shopping on Corey Avenue.