Vacation rentals with a pool in South Pasadena

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Top-rated rentals with a pool in South Pasadena

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favourite
Condo in Sunset Beach
4.96 out of 5 average rating, 161 reviews

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!

Top guest favourite
An aerial view captures the waterfront community, highlighting the proximity to the beach and nearby amenities. Serene blue waters of the canal intertwine with the residential buildings, while the expansive shoreline stretches in the background, offering a picturesque setting for relaxation and exploration.
Condo in Treasure Island
4.98 out of 5 average rating, 149 reviews

Beach, dolphin/manatee sightings, fishing, sunsets

Welcome to the newly remodeled condo in the Heart of Treasure Island. This bright and modern retreat is perfect for relaxing and avoiding the crowds. Perfect location for beach lovers and wildlife watchers alike with waterfront views of the canal from the living room, kitchen and bedroom windows and beautiful sunsets. Just 2 blocks or a 5 minute walk to the beautiful white sandy beach and a few feet from the canal and pool. Visit nearby great restaurants, John's Pass Boardwalk and live music.

Top guest favourite
A private balcony offers a serene view of the bay, framed by lush palm trees. A glass table and two chairs are positioned for easy enjoyment of the surroundings, while the sparkling water glimmers under a clear blue sky.
Condo in St. Petersburg
4.96 out of 5 average rating, 275 reviews

Waterfront Condo w/ Pool & Hot Tub! Mins to Beach!

This unit is completely updated and modern! Enjoy a GORGEOUS view from the 20' private balcony overlooking the Bay, pool and hot tub! Watch dolphins every morning while sipping your coffee, or while enjoying a glass of wine in the evening! A 6-minute drive to Madeira Beach, and close to all amenities with many restaurants nearby, including Doc Ford's next door, and shopping within 7 minutes. Lots to do; close to fishing including deep sea, and jet skiing. 1 bedroom, sleeps 4; comfy pull-out.

Top guest favourite
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
4.99 out of 5 average rating, 209 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.

Top guest favourite
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.
Guesthouse in Central Oak Park
4.98 out of 5 average rating, 234 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 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 favourite
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 homes in Gulfport
4.96 out of 5 average rating, 136 reviews

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!

Guest favourite
A serene waterfront view is offered from the balcony, featuring a round table with two chairs. Palm trees frame the view, while calm waters reflect the clear sky, creating a peaceful outdoor space perfect for relaxation.
Condo in St. Petersburg
4.81 out of 5 average rating, 215 reviews

🏝🏝Charming Bayfront Condo at Boca Ciega

This lovely waterfront condo located in wonderful Boca Ciega Resort in St. Petersburg, FL has everything you need for an extended stay. Centrally located with great views and amenities. Enjoy the sunset and gorgeous views whether it’s inside while lounging on the sofa or outside on the balcony. It sleeps up to 3 people (one bedroom and a sofa in the living room). Full kitchen, TV in living/bedroom, WiFi, and close proximity to the best beaches Florida has to offer.

Top guest favourite
Apartment in St. Petersburg
4.94 out of 5 average rating, 124 reviews

Waterfront studio! Heated pool and hottub

Wake up to stunning waterfront views! Unwind in this bright studio overlooking Boca Ciega Bay, sip coffee on your private balcony while watching dolphins. Highlights: • Direct waterfront views from balcony • Heated pool, spa & fitness center overlooking bay • Minutes to Madeira Beach, St. Pete, & War Veterans’ Memorial Park • Cozy king bed • Close to boat rentals, trails, and waterfront dining Perfect for romantic getaway or peaceful solo escape!

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
4.76 out of 5 average rating, 178 reviews

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!

Top guest favourite
A modern living space is presented with light-colored tile flooring and large glass doors providing access to the pool area. Soft blue curtains frame the doors, while a grey sofa and sleek entertainment unit add to the contemporary design. A ceiling fan circulates air in the room.
Guesthouse in Central Oak Park
4.99 out of 5 average rating, 118 reviews

Villa Splash, 1 room pool suite

Tropical pool villa in central St Pete built in 2022, only 1 mile from Pinellas Trail, 2 miles from downtown restaurants and 5 miles from Treasure Island Beach. One room efficiency includes a comfortable queen size murphy bed, full bathroom (w/shower-no tub), large flat screen tv, with wet bar, microwave & coffee maker. Guests will have private access to pool. Smoking is NOT permitted on property and will be reported.

Top guest favourite
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.
Apartment in Treasure Island
4.93 out of 5 average rating, 153 reviews

Beachfront Condo w/ Ocean View - Newly Renovated!

Newly renovated, 4th floor beachfront condo with a private balcony overlooking the gulf on Treasure Island Beach within walking distance to beaches, onsite pool, bars, and restaurants. View the sunset from your condo where you can relax in a queen size bed, full size sofa bed, and single fold up cot. Inside is a combo living/dining area and fully equipped kitchen, surrounded by beautiful furnishings and art.

Top guest favourite
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.
Guest suite in St. Petersburg
5 out of 5 average rating, 169 reviews

Suite Retreat in Southwest St. Petersburg

Cozy suite just 10 minutes to beaches or to vibrant downtown St. Petersburg. Parking on the premises. Relax in your private quarters supplied with plenty of creature comforts that make you feel like you are in your home away from home. Comfortably laid out living and dining area; kitchenette, bathroom, and bedroom with French doors leading you out to the pool.

Popular amenities for South Pasadena rentals with a pool

When is the best time to visit South Pasadena?

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Avg. price$226 CAD$301 CAD$349 CAD$273 CAD$239 CAD$226 CAD$231 CAD$212 CAD$202 CAD$207 CAD$207 CAD$228 CAD
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Quick stats about vacation rentals with a pool in South Pasadena

  • Total vacation rentals

    Explore 230 vacation rentals in South Pasadena

  • Nightly prices starting at

    South Pasadena vacation rentals start at $95 CAD per night before taxes and fees

  • Verified guest reviews

    Over 10,810 verified reviews to help you choose

  • Family-friendly vacation rentals

    100 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wifi availability

    230 of South Pasadena vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across South Pasadena rentals

  • 4.8 Average rating

    South Pasadena stays are highly rated by guests—averaging 4.8 out of 5!

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