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, 203 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.

4.97 out of 5 average rating, 144 reviews

A cozy living area features a comfortable gray sofa and a blue accent chest. Large glass doors open to a balcony, showcasing water views. A ceiling fan provides a gentle breeze, while decorative elements like wall art and a rug add a touch of charm.

Condo in St. Petersburg

Waterfront condo w heated pool and hottub

Wake up to waterfront views! Sip morning coffee on 20-ft private balcony overlooking Boca Ciega Bay, watch dolphins, unwind in the heated pool & spa while taking in stunning sunsets. This quiet corner condo offers a serene escape minutes from Madeira Beach, St. Pete, and local attractions, perfect for couples or solo travelers. Highlights: • Direct waterfront views • Heated pool, hot tub • Nearby boat rentals, trails, & Madeira Beach • 5 mins to Gulf beaches + 15 mins to Downtown St. Pete

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!

A spacious outdoor entertainment area features a tropical saltwater pool surrounded by a screened enclosure. Colorful loungers in vibrant pink and green are positioned near the pool, complemented by a dining table. A shaded area offers comfort for relaxing in the sun.

4.91 out of 5 average rating, 400 reviews

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!

Vibrant 2BR/1Bath home sleeps 8 guests with a magical outdoor space designed to create beautiful memories! A tropical saltwater pool and large covered entertainment area complete with a TV—perfect for relaxing and enjoying a cocktail. The interior is colorfully curated to embody the essence of a vacation! Located just 5 minutes from the beach and 25 minutes to downtown. We have 16 Airbnb homes (family-owned and operated), and we're dedicated to finding the perfect fit for your getaway.

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!

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 out of 5 average rating, 185 reviews

Beautiful Tampa Bay Pool Home Near Gulf Beaches

A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

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, 371 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.

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.

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.

4.98 out of 5 average rating, 143 reviews

A spacious living area features a sectional couch and a decorative area rug, enhancing the inviting ambiance. A dining table with modern chairs is positioned against a striking patterned accent wall, while natural light filters through the nearby windows, casting a warm glow over the space.

Home in Pinellas Park

Insta Worthy Retreat -Arcade Games- Htd Pool- Golf

Looking for a place the whole family/group can enjoy? This centrally located MODERN house is not only full of fun and style but equipped with everything you could need. Think of it as your true home away from home. Guests will love the Instaworthy Retreat with features like 5 hole mini golf, giant outdoor games, a heated pool, 5000 arcade games and of course, photo ops. Located 6 miles to the beach or Downtown St. Pete this home is the perfect place to getaway.

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

4.97 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

Superhost

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

4.89 out of 5 average rating, 120 reviews

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

A screened-in pool area features a uniquely shaped pool with clear blue water, inviting relaxation. Sunlight filters through the mesh covering, illuminating the surrounding patio. Lush greenery lines the background, enhancing the outdoor ambiance.

4.98 out of 5 average rating, 163 reviews

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

4.95 out of 5 average rating, 133 reviews

A spacious living area is highlighted by large glass doors that open to the pool area. The room features modern furnishings, including a comfortable gray sofa and a hanging chair, with natural light enhancing the neutral decor.

Home in Seminole

Lavish Heated Saltwater Pool Home Mins. to Beach

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

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

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

4.93 out of 5 average rating, 212 reviews

Condo in St. Pete Beach

850 Sqft - 1 Bedroom 1.5 Bath (GULF FACING!) Condo

A bright Florida room features large windows providing views of the water and marina. The space is equipped with a round table and two chairs, accented by orange cushions. Sunlight fills the room, creating a warm and inviting area for relaxation.

4.84 out of 5 average rating, 107 reviews

Intercostal Hidden Gem Beach Pool & Dock Fish'n

4.96 out of 5 average rating, 112 reviews

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.

Condo in St. Pete Beach

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

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

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.

4.99 out of 5 average rating, 141 reviews

Beach, dolphin/manatee sightings, fishing, sunsets

Other holiday rentals with a pool

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

Cottage in Historic Old Northeast

Two chairs in green and blue are positioned on a sandy area overlooking calm waters. The image features a distant pier with a modern structure, framed by a clear blue sky, enhancing the serene coastal ambiance.

5 out of 5 average rating, 21 reviews

Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bike

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

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.

5 out of 5 average rating, 9 reviews

Paradise Palms - Private Pool Oasis - St. Pete

Guesthouse in Historic Kenwood

A serene outdoor space features a curved pool surrounded by tropical plants. Lounge chairs are positioned near the water, alongside a shaded area with an umbrella. A guest house can be seen in the background, complementing the vibrant greenery and inviting setting.

5 out of 5 average rating, 65 reviews

Kenwood Cottage