Vacation rentals with a pool in South Pasadena

5.0 out of 5 average rating, 102 reviews

Glorious Sunsets - Beachfront 2BR Condo

Your perfect getaway on the stunning shoreline of Sunset Beach where soft sand, shimmering waters, and sunsets are part of every day. This spacious unit offers all the comforts and amenities you’d expect, with plenty of room to relax, unwind, and make yourself at home. Just a short walk to laid-back beach bars, restaurants, and live music. Iconic John’s Pass Village is a short drive, where you can enjoy dolphin and sunset cruises, fishing charters, jet ski & boat rentals, shopping, and dining.

4.97 out of 5 average rating, 140 reviews

A Perfect Condo Near The Beach

Enjoy this renovated 1st floor condo with a private patio, just an 11-minute walk to the beach! Close to fabulous restaurants, water sports, Sunset Beach, and the historic Corey Ave shopping district. This ground-floor condo has everything you need, including a large updated kitchen. We have access to a pool for guests of the complex, and the park across the street has courts for pickleball or tennis, a boat ramp, and a gazebo overlooking the water. Treasure Island is just around the corner!

Superhost

4.87 out of 5 average rating, 134 reviews

Inground Pool w/ Game Room - Fully Renovated House

Beautifully remodeled 3 bedroom 2 bath farmhouse with INGROUND POOL in the heart of Gulfport. Looking for the BEACH?(St Pete Beach, Treasure Island etc) We are 6 mins away! If you are looking for amazing restaurants and bars in the middle of St Petes we are only 10 minutes to DOWNTOWN! If your are here for some baseball we are 15 minutes away from Tropicana field and St Pete Pier! If you are looking to explore In clearwater or Downtown Tampa we are only 25 minutes away including TAMPA Airport!

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.

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.

4.8 out of 5 average rating, 211 reviews

Beautiful 2bd 2ba Condo Minutes to Beach/Heat Pool

EVERYTHING IS NEW!!! This spacious newly updated and newly furnished condo with smart Tv's in every room, spectrum cable and high speed internet is all you need for your perfect vacation! We are just 0.6 miles, short 10 minutes walk or 1 minute drive to the beach. Walk to Caddy's on the beach, John Pass Village( 6 min drive), drive to Downtown St Pete for night life or nice dinner. Egan park is very close and tennis courts are right across the street. Heated pool and laundry in the building

4.99 out of 5 average rating, 110 reviews

A well-lit kitchen is equipped with wooden cabinets and a spacious countertop. Three white bar stools are arranged at the island, which is adorned with a vase of fresh flowers and a platter. Large windows allow natural light to brighten the room.

Home in St. Pete Beach

Gulfside Resort: 3 bed, 2 bath /pool access

Welcome to GulfSide Resort, a family-owned gem just a block and a half from St. Pete Beach! Our comfortable vacation suites face a beautiful pool and are a short stroll away from beach bars, restaurants, and shopping. Enjoy our pool, shuffleboard, and putting green, plus complimentary beach chairs and toys. Perfect for group gatherings, we can host up to 35 guests comfortably. Experience relaxation and fun with your loved ones at GulfSide Resort—your ideal vacation spot! The house sleeps 6.

4.97 out of 5 average rating, 146 reviews

St Pete Retreat WalktoBEACH*HeatedPOOL*PrivateYARD

Come enjoy this getaway vacation home on St Pete Beach!! A one of a kind, fully renovated beach house with pool and private backyard, to provide you with a luxurious yet cozy place to stay. In prime location on St. Pete beach, and a short walk to Treasure island beach! A vacation here offers comfort at home, relaxation at the beach, fun filled outdoor activities (biking, tennis, boat rentals), all while enjoying the vibrant St Pete Beach scene full of amazing beach restaurants and bars.

4.95 out of 5 average rating, 168 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!

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, 190 reviews

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 exterior of the Ocean Club building is showcased, featuring a modern design with a white façade and large balconies. Palm trees line the front, enhancing the tropical setting. A welcoming entrance is visible, set against a backdrop of a bright sky with soft clouds.

Condo in Treasure Island

Beachfront Condo in Exclusive Resort

The most stunning views from this brand new condo directly on Treasure Island Beach. This lovely unit is on the 4th, 5th, or 6th floor and provides sweeping views of the ocean. This units has 2 bedrooms and 2 full bathrooms. The inviting open concept living area has one of the best views of the ocean, especially when the retractable sliding doors are opened. The dining table on your private balcony provides a perfect dining area, with the ocean providing a beautiful backdrop.

4.86 out of 5 average rating, 674 reviews

A bright kitchen showcases modern appliances, including a stove, microwave, and refrigerator, complemented by a granite countertop. A small island adds functionality, while a dining table with two chairs offers seating. Cheerful yellow walls create a lively atmosphere, contrasting with the subtle blue accents.

4.84 out of 5 average rating, 118 reviews

Sunset Beach Cozy Private Condo

This is the place to relax and unwind. Gorgeous Sunset Beach on Treasure Island has miles of white sugar sand beaches and sparkling gulf water. One of the best kept secrets on the Gulf Coast. The condo is one bedroom, one bath on the second floor. Just steps away from the beach. The first floor units are currently under construction due to Hurricane Helene damage. You are walking distance to the world famous Caddys beach restaurant, Kai Tiki, and Taco Bus

Superhost

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

THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!

4.76 out of 5 average rating, 218 reviews

Popular amenities for South Pasadena rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 170 reviews

A serene outdoor space features a heated pool surrounded by several lounge chairs and an umbrella for shade. Lush green plants and a wooden privacy fence complement the vibrant color of the cottage in the background, enhancing the inviting atmosphere.

Home in Gulfport

Bungalow Heated Pool Home 10 minutes to Beaches

4.94 out of 5 average rating, 189 reviews

Home in Gulfport

Retro Disco Pool Home Near St Pete Beach

4.98 out of 5 average rating, 102 reviews

Pet Friendly Pool Oasis St Pete/Gulfport

A spacious backyard is highlighted by a solar heated pool, surrounded by lush greenery and native plants. Comfortable lounge chairs face the water, with colorful floatation devices resting nearby. A shaded area is provided by a patterned umbrella, offering a spot to relax and enjoy the scenery.

4.99 out of 5 average rating, 142 reviews

Mad Beach HideAway • Private Pool • 4 Bed • 3 Bath

4.98 out of 5 average rating, 192 reviews

Home in Pinellas Park

Insta Worthy Retreat -HTD Pool- Arcade Room- Golf

4.96 out of 5 average rating, 184 reviews

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

A private backyard features a custom-made pool surrounded by a wooden deck. Lounge chairs and a sun umbrella are positioned nearby, while palm trees and lush greenery offer a tropical ambiance. A white privacy fence encloses the space, enhancing the serenity.

5.0 out of 5 average rating, 229 reviews

Beautiful Tampa Bay Pool Home Near Gulf Beaches

4.97 out of 5 average rating, 116 reviews

Heated Pool l BBQ | Karaoke | Outdoor Projector

Condo rentals with a pool

4.96 out of 5 average rating, 191 reviews

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

4.87 out of 5 average rating, 169 reviews

A spacious studio features a king-sized bed adorned with a patterned comforter. A cozy seating area includes a light-colored sofa and a small table. Large glass doors offer direct oceanfront views, with a balcony visible in the background, allowing natural light to fill the space.

Condo in Treasure Island

Treasure Island Studio | Gulf Views & Pool

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, 249 reviews

St. Pete Beach Condo • Heated Pool • Walk to Beach

The outdoor pool area, surrounded by palm trees, features a clean, inviting pool with lounge chairs positioned around it. In the background, the beach can be seen, with soft white sand meeting the clear ocean waters.

4.86 out of 5 average rating, 281 reviews

Gulf Strand Beach Resort

A sandy pathway, framed by lush green grass, leads to the beach where the ocean meets the sky. Soft clouds drift above, and the vibrant blue water sparkles in the sunlight, creating an inviting atmosphere for beachgoers.

4.88 out of 5 average rating, 392 reviews

Easy access to St. Petersburg beach, a minute walk

A bright bedroom features a spacious bed adorned with light blue and white striped linens. Natural light floods the room through sliding glass doors that lead to a private balcony with an ocean view. Two decorative lamps and a textured area rug enhance the serene atmosphere.

4.89 out of 5 average rating, 160 reviews

2 Story Penthouse | Pool | Balcony | Gulf View 602

An aerial view captures the coastline of St. Pete Beach, showcasing a long stretch of sandy beach lined with beach chairs. Nearby, residential and commercial buildings are visible, along with flowing roads and vibrant greenery that enhance the local landscape.

4.95 out of 5 average rating, 146 reviews

Upham Beach-Paradise in St. Pete Beach & Parking!

A wooden boardwalk leads towards the beach, illuminated by a warm sunset reflecting off the ocean waves. The sky features shades of orange, pink, and purple, creating a serene backdrop for the tranquil atmosphere inviting visitors to the shore.

4.93 out of 5 average rating, 168 reviews

Beach getaway on the beach

Other vacation rentals with a pool

Apartment in Treasure Island

An inviting living area features a light gray sofa and a round white coffee table. Large glass doors open to a private balcony with unobstructed views of the Gulf of Mexico, creating a seamless connection with the beachfront landscape.

Beachfront Condo w/ Ocean View - Newly Renovated!

4.94 out of 5 average rating, 197 reviews

Apartment in St. Petersburg

Waterfront studio! Heated pool and hottub

4.95 out of 5 average rating, 149 reviews

4.99 out of 5 average rating, 243 reviews

The kitchen features navy blue cabinets, providing a stylish contrast to the stainless steel appliances. A spacious countertop holds essential kitchen gadgets, and a modern backsplash adds texture. Adequate storage is available with cabinets and drawers, contributing to a well-organized cooking space.

Condo in Madeira Beach

Rincón Divino MB 2 Balconies, Ocean & Marina Views

Vacation home in South Pasadena

Heated Pool Oasis 4BR Sun-Kissed Retreat+ Fire Pit

4.92 out of 5 average rating, 48 reviews

4.92 out of 5 average rating, 38 reviews

Luxury St Pete Pool Home-2.6mi to beach-Jetted Tub

5.0 out of 5 average rating, 29 reviews

Home in Treasure Island

Waterfront Condo with Boat Slip & Fishing Dock

A cocktail pool is framed by tropical landscaping, featuring vibrant pink flowers in the foreground. Shady umbrellas provide coverage around the pool area, with palm trees and lush greenery creating a serene, inviting environment for relaxation.

4.99 out of 5 average rating, 80 reviews

Relax@ Palm Pool Guesthouse • 5 Min St. Pete Beach

An outdoor space features a stylish lounge area with two chaise lounges placed on a wooden deck. A large umbrella offers shade over a table. The backdrop includes a resort-style pool, surrounded by palm trees, as a sunset paints the sky in soft hues.