Holiday rentals with a pool in St. Petersburg

4.95 out of 5 average rating, 142 reviews

Condo in Sunset Beach

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!

Guesthouse in St. Petersburg

A charming yellow cottage is framed by lush palm trees and tropical plants, featuring a welcoming front door at the end of a paved walkway. Sunlight filters through the greenery, creating a bright and inviting atmosphere near the entrance.

4.9 out of 5 average rating, 140 reviews

St Pete Casita Studio with Salt Water Pool & Yard

Keep it simple at this peaceful and centrally-located place. La Casita is located minutes from bustling downtown and beautiful bay waterfront restaurants and bars. Tampa International Airport is only 20 minutes away. The property itself is great for relaxing. La Casita is surrounded by lush palm trees and has its own access to the pool a few feet from your front door. Come relax, go to the pool, beach, enjoy the outdoor shower and finish off the day at One of the many nearby restaurants!

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, 204 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.

Guesthouse in Central Oak Park

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!

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!

Guest suite in St. Petersburg

A spacious patio area surrounds a clear swimming pool, framed by lush tropical plants. Two lounge chairs are positioned under a shaded umbrella, with a bike resting in the background. A barbecue grill is visible near the covered seating area, creating an inviting outdoor space.

4.98 out of 5 average rating, 372 reviews

Cozy Casita in NE St. Petersburg

Our Cozy Casita is located adjacent to the main house in a quiet residential neighborhood with a separate entry and fenced in parking space for our Guests. Enjoy our tropical garden and beautiful pool area. The pool is not heated. Small kitchen with Whirlpool electric stove, microwave and mini-fridge. 40” Samsung Smart HDTV and WIFI. Located within minutes of great restaurants, craft breweries, and local museums. Lots of great outdoor activities along St. Pete’s beautiful waterfront.

4.98 out of 5 average rating, 196 reviews

SPARKLING HOT Modern Pool Home- Minutes to beach!

This recently remodeled home features 4BR/3BA, including a charming poolside guest bungalow. The interior design is a showstopper—photos don’t do it justice! Enjoy a dream kitchen and saltwater pool overlooking a lake teeming w/ wildlife. Smart TVs in every room and outside (with WiFi)! Located just 8 minutes from the beach in a family-friendly neighborhood near dining and shopping. Professionally cleaned for a pristine stay. Heated pool option available for an extra cost. Book now!

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.

4.89 out of 5 average rating, 140 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.

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, 156 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.

4.98 out of 5 average rating, 278 reviews

A serene balcony offers a view of the waterfront, with two green chairs and a glass table positioned to enjoy the scenery. Palm trees are visible in the foreground, and the calm water reflects the bright blue sky, creating a tranquil outdoor space.

Condo in St. Petersburg

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

My place is across the street from Target and many restaurants within walking distance. There is a PSTA Bus stop right at the entrance to the condo property.Uner and Lyft are availablThe Pinellas Trail is across the street. The VA Hospital and Bay Pines Park are biking or walking distance. The closest beach is Madeira Beach 2 miles from the condo. All Utilities, Cable/Internet are included. Parking is free and close to the elevators. Plenty of parking spaces are available also.

Apartment in St. Petersburg

4.94 out of 5 average rating, 113 reviews

Private balcony & heated pool hottub condo

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!

Apartment in Historic Old Northeast

A well-lit bedroom features a spacious bed adorned with striped bedding. Built-in maple cabinetry offers storage and a workspace, complemented by a large black countertop. Light streams through several windows, enhancing the airy feel of the room.

4.83 out of 5 average rating, 342 reviews

Luxury studio in a jungle

This comfortable, private apartment is located above the detached garage of a restored 1930 house situated on a triple lot in one of the best neighborhoods in town. It's very close to lively downtown St. Pete, yet very quiet and private. The koi pond with cascading waterfalls is one feature of the lush jungly yard with pool and hot tub. A new 55" Samsung smart TV has just been installed. Enjoy Spectrum cable or sign into your streaming services.

Popular amenities for St. Petersburg rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 135 reviews

An aerial view captures a spacious patio surrounding a custom saltwater pool, where lounge chairs are arranged alongside. Lush landscaping features palm trees and flower beds, while a covered seating area, equipped with outdoor furniture, is visible behind the pool. The home showcases a modern design with a sleek metal roof.

Home in Seminole

Tootsie’s Beachside Retreat

4.99 out of 5 average rating, 119 reviews

A covered patio area features a built-in seating arrangement with soft cushions, accompanied by a round coffee table. The space opens to a sparkling pool surrounded by wooden decking and lush greenery, offering a serene outdoor experience.

Home in Tampa

Hacienda Hideaway w/ heated pool

4.97 out of 5 average rating, 160 reviews

A cozy outdoor fire-pit area is surrounded by colorful seating. Decorative stones cover the ground, leading to a grill and the inviting glow of flames. A pool and shaded area can be seen in the background, set against a twilight sky.

Home in Clearwater

Fun, Funky, Pool, Fire Pit! 4 miles to Beach

4.98 out of 5 average rating, 138 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

4.89 out of 5 average rating, 120 reviews

A rectangular heated pool is surrounded by a screened enclosure, featuring inviting blue water and colorful inflatable pool toys. Lounge chairs are positioned along the edge, with a light brown paver patio enhancing the outdoor space. Lush greenery is visible in the background.

Home in Clearwater

Family Fun! Heated Pool/Arcade/Foosball + 2 Kings

Superhost

An inviting pool area is enclosed with a screen and features a unique shape. Clear water reflects the serene surroundings, while soft lighting hangs above. The patio is surrounded by a neat fence, ensuring privacy, and potted plants add a touch of greenery.

4.83 out of 5 average rating, 129 reviews

Beautiful & Exclusive house + Pool!

4.94 out of 5 average rating, 127 reviews

Home in Largo

Swim-Out Bedroom, Waterfall pool! The Peace Place

4.95 out of 5 average rating, 118 reviews

An inviting outdoor space features a heated pool and a shaded area adorned with cafe lights. Two hanging egg chairs and comfortable seating arrangements complement the modern wooden furniture. The stylish striped rug enhances the atmosphere, while the pool's tranquil blue water is visible in the background.

Home in Largo

Palm Paradise - Family Amenities+Central Location

Condo rentals with a pool

4.97 out of 5 average rating, 132 reviews

Condo in Clearwater

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

4.99 out of 5 average rating, 211 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

Lux Condo w/ 2 balconies, Ocean & Marina views

Superhost

A spacious living area is illuminated by natural light from large windows. Two sofas, one being a sleeper, are arranged around a circular glass table. The kitchen area features wooden cabinetry with a black countertop, while decorative wall frames provide a subtle touch.

Condo in St. Pete Beach

4.83 out of 5 average rating, 250 reviews

Amazing condo minutes to the beach*** heated pool

An outdoor seating area is shown with a glass-top table surrounded by four blue chairs. Two charcoal grills are positioned nearby under palm trees, with a view of the water in the background. The screened cabana features a thatched roof, providing a relaxing atmosphere.

4.91 out of 5 average rating, 163 reviews

Waterside Studio in the heart of TI, walk to beach

A serene beach scene features four white benches set in soft sand, facing a vibrant sunset over the Gulf. Lush green foliage and pathways lead to the shoreline, creating a natural and inviting outdoor space.

4.93 out of 5 average rating, 136 reviews

Beachfront w/ Stunning Sunsets in Prime Location.

4.89 out of 5 average rating, 175 reviews

A modern living area features a gray sofa adorned with colorful pillows. A white coffee table is placed on a soft area rug. Large sliding glass doors provide direct views of the waterfront, while palm trees can be seen just outside, enhancing the tropical ambiance.

Condo in Tampa

Luxury Blue Haven - Stunning Tampa Bay Views!

4.94 out of 5 average rating, 117 reviews

A spacious bedroom is equipped with a king-size bed, complemented by nightstands with lamps. A flat-screen smart TV is mounted on the wall. Artwork adorns the walls, and natural light filters through the windows, offering a view of the pool area from the ground floor.

Condo in Clearwater

By the POOL, Ground floor, King bed, NO PETS

4.95 out of 5 average rating, 332 reviews

A serene balcony view captures a sunset over calm waters, with silhouetted palm trees in the distance. A small round table with a lantern sits next to a comfortable chair, creating an inviting space for relaxation.

Condo in Tampa

Modern Waterfront Condo - Captivating Sunset Views

Other holiday rentals with a pool

4.97 out of 5 average rating, 59 reviews

A serene outdoor space features a glimmering swimming pool surrounded by lush greenery. Comfortable lounge chairs with colorful cushions are positioned on a decorative rug. A playful float and playful decorations enhance the inviting atmosphere, while a small shed is visible in the background.

Home in Gulfport

Modern studio, pool & patio | 10 min to DT & BEACH

4.95 out of 5 average rating, 66 reviews

King / Child Friendly / Near DT / No Chores!

A newly renovated outdoor area features a tranquil swimming pool surrounded by stone tiles and lush tropical plants. The bright blue water reflects the sunny sky above, while a dining table is positioned nearby, enhancing the welcoming environment of the space.

5 out of 5 average rating, 23 reviews

Modern Coastal Retreat

5 out of 5 average rating, 9 reviews

The outdoor area showcases a heated private pool surrounded by a stone patio. A cozy seating area is positioned under a covered porch. A giant ring toss game stands next to the pool, while lounge chairs and an umbrella provide options for relaxation.

Home in Pinellas Park

Coastin' Close Family Fun~HTD Pool~Outdoor Games

Guesthouse in St. Petersburg

A tranquil outdoor space features a private saltwater pool surrounded by stone pavers and lush tropical landscaping. Comfortable seating areas are arranged under an umbrella, while string lights provide soft illumination. A pergola offers additional shaded seating, enhancing the inviting atmosphere.

5 out of 5 average rating, 44 reviews

Coquina Keys Guest House

Guesthouse in Crescent Lake

A serene outdoor space features a saltwater pool surrounded by lush greenery. Two lounge chairs are positioned under a striped umbrella, providing shade on the pool deck. The light-colored stone tiles enhance the calming atmosphere of this private retreat.

5 out of 5 average rating, 13 reviews

Luxury Pool House

Apartment in Edge District

4.92 out of 5 average rating, 48 reviews

Tropicana Stadium 2 Bed In DWTWN W/ Free Parking

A contemporary home is presented with a light-colored exterior and a stylish wooden garage door. Lush greenery and palm trees enhance the landscape. A spacious driveway leads to the entrance, framed by well-maintained flower beds and tropical plants under a clear blue sky.