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.

4.87 out of 5 average rating, 131 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!

The spacious living area features a blue sofa with decorative pillows, a white coffee table, and a dining space with a round table and four chairs. A ceiling fan circulates air, and the kitchen is visible in the background, complemented by light-colored cabinetry.

4.92 out of 5 average rating, 177 reviews

Updated Condo minutes from the beach - heated pool

Welcome to this fabulous and spacious newly updated condo close to the beach and many restaurants. Closest beach is 12 min walk or 2 min drive. John Pass Village is only 6 minutes drive, Downtown St Pete and newly re-opened St Pete Pier is a must visit for either night life or nice dinner. Egan Park and tennis courts are across the street. Pool is in the building- hours of operation is from dusk to down.Pool is heated to 82f during the day. Roku TV's in bedroom and 65" Smart Tv in living room

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.

4.99 out of 5 average rating, 231 reviews

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.

4.99 out of 5 average rating, 109 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.

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, 158 reviews

2 Story Penthouse | Pool | Balcony | Gulf View 602

This luxury penthouse suite has been freshly remodeled and includes a direct, panoramic ocean view! The direct Gulf views are STUNNING, best on the island guaranteed. You will have direct pool and beach access. This two story condo has a townhouse layout with a private balcony on the second floor. Walking distance to local restaurants and bars. You are a short drive to St. Johns Pass, Clearwater, Fort Desoto State park and downtown St. Pete! 6 guest limit and no smoking strictly enforced.

4.97 out of 5 average rating, 143 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.

4.88 out of 5 average rating, 142 reviews

Renovated 2BD Beach Getaway in Prime Location!

Walk to waterfront restaurants, bars, and white sandy beaches all within 15 mins. Perfect home base for your vacation! This bright ground floor 2BR/2BA condo has been renovated from top to bottom sleeping 4. We're excited to be able to share our home again after the completion of our renovations following the Hurricane in 2024. Our place has the largest, private patio —steps from the pool - and many extras such as beach chairs, umbrella, kitchen appliances, and more for you to enjoy.

4.95 out of 5 average rating, 164 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.

4.9 out of 5 average rating, 187 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.

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.

4.89 out of 5 average rating, 246 reviews

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

Relax in this bright, first-floor beach condo just a 4-minute walk to St. Pete Beach. Enjoy a full kitchen, king bedroom, washer/dryer in unit, fast WiFi, and a comfy living area with a sleeper sofa. The gated community offers a heated pool, grilling area, and free parking. Beach chairs, beach towels, and umbrellas are included—everything you need for an easy, comfortable getaway. Walking distance to many restaurants and shops, making this the perfect location!.

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, 215 reviews

Popular amenities for South Pasadena rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 102 reviews

Pet Friendly Pool Oasis St Pete/Gulfport

4.98 out of 5 average rating, 189 reviews

Home in Pinellas Park

Insta Worthy Retreat -HTD Pool- Arcade Room- Golf

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, 227 reviews

Beautiful Tampa Bay Pool Home Near Gulf Beaches

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, 140 reviews

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

4.97 out of 5 average rating, 242 reviews

Coastal Pool Retreat *5 Min to Madeira Beach Sand

4.98 out of 5 average rating, 234 reviews

Home in Clearwater

Specious home W/ Heated Pool ! ! ! Great Location.

5.0 out of 5 average rating, 27 reviews

Home in South Pasadena

Waterfront/ Sunsets/ Heated Pool/ Tiki Bar/ Dock

5.0 out of 5 average rating, 26 reviews

Home in South Pasadena

Mangrove Haven | Pool + Hot Tub + Waterfront Dock

Condo rentals with a pool

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.

4.89 out of 5 average rating, 214 reviews

Beachfront Condo Resort on Treasure Island

4.97 out of 5 average rating, 236 reviews

*Shore Thing* Walk to Beach | Intercoastal Views

4.93 out of 5 average rating, 109 reviews

Condo in Tierra Verde

Island Escape • Pool • Jacuzzi • Minutes to Beach!

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

4.96 out of 5 average rating, 188 reviews

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

4.93 out of 5 average rating, 134 reviews

Waterfront Condo With Pool and Multiple Views!

A modern kitchen area features a large island with seating, complemented by white cabinetry and gleaming countertops. Natural light floods the space through expansive sliding glass doors, which lead to a private terrace with ocean views. A comfortable seating area is arranged nearby.

4.91 out of 5 average rating, 117 reviews

Luxury Seashell Oceanfront Condo with Pool

4.99 out of 5 average rating, 240 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

Other vacation rentals with a pool

Apartment in Treasure Island

A living area features a comfortable blue pullout couch, two wicker chairs, and a round dining table. A modern flat-screen TV is mounted on the wall, while light streams through a window adorned with sheer curtains, enhancing the spacious feel of the room.

Molloy Poolside Suite - 2 Full

4.8 out of 5 average rating, 177 reviews

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

4.99 out of 5 average rating, 182 reviews

Vacation home in South Pasadena

Heated Pool 4BD 3BA| Near St. Pete Beaches +Dining

4.91 out of 5 average rating, 47 reviews

4.96 out of 5 average rating, 68 reviews

Home in Gulfport

*POOL* Fenced Yard *Shuffleboard Court*

4.9 out of 5 average rating, 70 reviews

Waterfront Heated Pool + Private Dock + Near Beach

A spacious living room is featured, with a cozy seating arrangement including a light-colored sofa and soft armchair. A coffee table sits in the center, and a fireplace is positioned beneath a wall-mounted TV. Natural light floods in through large sliding glass doors leading to the outdoor area.

4.9 out of 5 average rating, 91 reviews

Sailfish Escape - Tropical Heated Pool Home

5.0 out of 5 average rating, 24 reviews

Home in Treasure Island

Waterfront Condo with Boat Slip & Fishing Dock