Vacation rentals with a pool in Upham Beach Park

A clear view of a refreshing pool surrounded by a fenced area. Sun loungers line the poolside, and a two-story building with multiple doors is seen in the background, framed by manicured greenery and palm trees.

4.93 out of 5 average rating, 107 reviews

5 STAR RENOVATED CONDO 3 MIN. WALK TO THE BEACH

3 min walk to beautiful St. Pete's Beach. Fully renovated condo has everything you need for the perfect getaway. Only 19 units in the building this is an oasis of relaxation. Great for the kids! Stunning pool, BBQ area, private laundry ensuite. Updated kitchen is fully equipped. Queen sized bed in the master and pull out couch in living room sleeps a total of 4. Two TVs and wifi. Parking for 2 cars. Walk to a great selection of restaurants, bars & transportation **No Pets and No Smoking please!

4.95 out of 5 average rating, 136 reviews

Condo in Treasure Island

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

NEWLY FULLY RENOVATED breathtaking beachfront condo on private beach. Walking distance to bars, restaurants, live music and more! Brand new king size bed, high speed wi-fi, Smart TVs with cable/Netflix, heated swimming pool, BBQ/Grills, outdoor tables, showers, beachfront balcony, workspace and you are RIGHT on the beach! Short drive to TPA/PIE airports, Downtown St Pete, Dali Museum & more! The condo is fully equipped with everything you need and run by a Superhost for a perfect Beach vacation!

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.

4.95 out of 5 average rating, 176 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.

4.99 out of 5 average rating, 201 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.

Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

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, 163 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.

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.

4.91 out of 5 average rating, 213 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

A pink, two-story building is prominently displayed with the 'Gulf Winds' sign in front. Lush palm trees frame the entrance, and a well-maintained white fence lines the walkway, providing a welcoming view of the resort's exterior.

4.91 out of 5 average rating, 166 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, 127 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!

4.88 out of 5 average rating, 139 reviews

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.

Home in St. Petersburg

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

Superhost

The modern condominium complex features multiple balconies overlooking a pool area. Vibrant tropical plants surround the pool deck, which is equipped with lounge chairs and shaded umbrellas. Clear blue skies and palm trees add to the inviting outdoor space.

Condo in Treasure Island

4.89 out of 5 average rating, 148 reviews

Beachfront Condo Resort on Treasure Island

Be among the first to experience this new condo resort. 992 sq ft of beachfront luxury with full resort amenities. These upper-floor corner units have gorgeous views of the ocean, and each room has a window with beach views. With 2 bedrooms and 2 bathrooms and a pullout couch in the living room, these units can comfortably house 6 people. After arriving in your open concept living area, you will access your private balcony through retractable sliding doors that let the ocean air in.

Superhost

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.

Apartment in St. Pete Beach

4.79 out of 5 average rating, 150 reviews

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 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.