Holiday rentals with a pool in Spring Hill

4.99 out of 5 average rating, 261 reviews

A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.

Home in Port Richey

Heated & Screened in Pool-All Essentials Provided

🏡 Private Pool House with Large Covered & Screened-In Porch Relax and unwind in this inviting private pool home, featuring a large covered and screened-in porch—perfect for enjoying the outdoors without the bugs. 🌊 Heated Pool Take a dip in the private pool, heated year-round with an electric heat pump (weather permitting), offering comfort no matter the season. Whether you're sipping coffee on the porch or enjoying a swim, this cozy retreat is ideal for a peaceful and private getaway.

An outdoor screened area features a private heated pool surrounded by a spacious deck. Two lounge chairs are positioned nearby, with a barbecue grill present for outdoor cooking. A dining set with multiple chairs is also visible under a covered patio, providing shade and comfort.

4.96 out of 5 average rating, 135 reviews

Weeki Wachee Springs heated pool home retreat

Relax with the whole family at this Weekie Wachee/Springhill Heated pool home. 5 minutes from the crystal clear springs of Weekie Wachee state park and Buccaneer Bay that has spring fed beach with water slides , tiki bars and mermaid shows. It’s also located 10-15 minutes from Rodgers Park located on the river where you can swim, kayak with manatees and enjoy fun family time! Also 15 minutes away is Pine Island Beach Park and SunWest Beach Park for skiing, wake boarding and obstacle course.

A heated private pool is surrounded by a screened enclosure, providing a bright and clear view of the outdoor space. Comfortable lounge chairs are positioned nearby, and the pool area is well-lit by natural sunlight filtering through the enclosure.

4.88 out of 5 average rating, 129 reviews

3BR Spring Hill Pool Home. Heated Pool & Hot Tub

Enjoy our beautiful pool home located In the heart of Florida's Gulf Coast! This 3BR/2.5BA home offers all amenities - screened enclosed private and heated pool, relaxing spa, pool table, large screen smart T.V'S, Free Netflix, fully equipped kitchen, private parking and more. Just minutes away from Commercial hwy and Cortez blvd where you will find plenty of restaurants, grocery stores and shops. Only 3 minutes from Weeki Wachee Springs State Park and 12 minutes to Pine Island Beach Park!

Apartment in Paradise Lakes

A modern living area features a light-colored sofa and dark accent chairs arranged around a central ottoman. A wall clock complements the artwork displayed above the couch, while the kitchen area is visible in the background, showcasing sleek cabinetry and appliances.

4.83 out of 5 average rating, 153 reviews

Millers, BeOne Naturally Clothing Optional Premium

Relax in your birthday suit in a fun clothing-optional Paradise lakes Resort. Modern furniture sleeps up to 4 People with a King Size Bed and a leather sleeper sofa in living room with Memory Foam mattress. Full kitchen with refrigerator, oven range and microwave for cooking, coffee maker, washer and dryer for laundry, 2 TVs, and a bath tub for relaxing. The clubhouse 2 Swimming Pools, Hot Tub, events like Karaoke, Live Bands and more (fees vary by days of week). Thank you and enjoy!

4.91 out of 5 average rating, 111 reviews

An aerial view showcases the property with a spacious pool integrated into the backyard. A well-maintained dock extends into the water, illuminated by a green light, accompanied by colorful kayaks. Nearby, palm trees add greenery to the inviting outdoor space.

Home in Hernando Beach

Waterfront home heated pool+jacuzzi+game room+golf

Bring your boat or rent nearby! Minutes to prime SCALLOPING waters. Enjoy a HEATED pool, jacuzzi, putting green, ping pong table, massage chair, arcade basketball, paddle boards, kayaks, bicycles, four jetski docks & boat dock. FISH CLEANING STATION/deep canal. Open floor plan with 3 BR, 3 BA and comfortably sleeps 16. Near boat ramp w/ access to Weeki Wachee springs. Great home for sunset cruises, scallops, dolphin &manatee watching, minutes to bike and hiking trails! Pet friendly!

4.91 out of 5 average rating, 141 reviews

The image captures an aerial view of a spacious two-story home in a serene setting. A pool is visible in the backyard, alongside a floating dock leading to a canal. Lush greenery and outdoor seating areas enhance the outdoor space.

Home in Hudson

Oasis Getaway

Relax with the whole family at this peaceful place to stay. Perfect Getaway with amazing sunset views from the upstairs balcony and a floating dock on a canal perfect for kayaking and manatee sight seeing. This canal will also take you straight to the ocean. Very spacious home with a tennis table located on the first floor and a beautiful pool to enjoy! Close to many attractions like Weeki Wachee Springs, Outdoor trails, a Marina, Water Park, Hudson Beach and great seafood restaurants.

Guest house in Spring Hill

A screened-in pool area is highlighted by a clear blue sky and scattered clouds. The pool, partially covered, is surrounded by light-colored pool decking. Lush greenery and palm fronds frame the scene, providing a relaxing outdoor space.

5 out of 5 average rating, 175 reviews

J&M Homestead

Relax with the whole family at this peaceful place to stay. Close to I-75 and Suncoast Parkway in Pasco County. Located north of Land O Lakes, Florida, in Pasco Trails, a gated community of acreage and horses. Outlet mall, many eating establishments and sports complexes within half-hour drive. We have had to institute a policy of "no smoking. To be clear, we are retired couple who live in the main house. The apartment is attached but has its own entrance and is self contained.

A spacious waterfront property is set on a canal, surrounded by greenery and palm trees. The structure features a large screened-in area, showcasing the outdoor living space and pool, while reflecting the tranquil water nearby.

4.87 out of 5 average rating, 114 reviews

PALM CREEK GETAWAY spring meets gulf+pool/spa

Enjoy natural spring yet only minutes kayaking to the gulf: 4BR, 3 full baths + living + dining + outdoor dining by screened & heated salt-water pool and spa ($30/nite extra) + screened patios. Get away to kayaking, scalloping, fishing, crabbing, biking, watching dolphins/manatees, fire pit, hammock in Florida sun... 5 mins drive to Weeki Wachee State Park, 7 mins drive to Pine Island, 30 mins to Homosassa, 1 hr to Tampa, 2 hrs to Disney. Close to restaurants, stores, grocery...

A screened-in pool area features a clear, inviting pool with a waterfall and soft blue water. Surrounding greenery provides privacy, while lounge chairs are positioned near the water. Sunlight filters through the mesh enclosure, creating a bright and airy atmosphere.

4.94 out of 5 average rating, 126 reviews

Spring Hill, Florida Quaint Paradise

The Retreat sleeps 4 guest comfortably. Our 2 bedroom, 2 bathroom home features a pool with a waterfall and fenced backyard. This quaint paradise will make you feel relaxed sitting by the pool enjoying a good book with a drink while you can hear the breeze going through the palms in the backyard. It’s located on a quiet street. But minutes away from different beaches, golf courses, shops and restaurants, attractions and parks.Something to do for the whole family.

Guest suite in Spring Hill

A green felt pool table occupies the foreground, with a set of colorful billiard balls arranged for a game. In the background, a screened-in patio reveals a tranquil pool surrounded by two lounge chairs, and views of the golf course beyond.

4.96 out of 5 average rating, 73 reviews

Attached Private GuestHouse- Fenced Yard

We are slowly working on creating a more environmentally friendly home, from solar energy to providing shelter and food for pollinators. Come and enjoy our slowly evolving oasis, whether it's bathing in the pool, relaxing in the jacuzzi (small charge for heating), or napping on the hammock. Weeki Wachee Springs State Park, Weeki Wachee River, & Pine Island Beach are all within 15-minute drive. Clearwater, Tampa, and Ocala are all within an hour's drive!

5 out of 5 average rating, 147 reviews

The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.

Home in Oldsmar

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

4.91 out of 5 average rating, 123 reviews

A private swimming pool is surrounded by a screened patio, with colorful floatation devices resting on the clear water. Lounge chairs are positioned nearby against a bright yellow wall. Natural light floods the area through glass doors, creating a refreshing atmosphere.

Home in Forest Hills

Heated Pool • Tarpon & Beaches

Oasis with a private pool heated Nov–Mar and a patio, 5 miles from Tarpon Springs, near Dunedin and a short drive to Clearwater/Tampa. Perfect for family or friends: fast Wi-Fi, workspace, fully equipped kitchen, and BBQ. 24/7 self check-in and on-site parking. Quiet for restful nights; beaches and parks minutes away. Note: pool heating available November–March (weather-dependent). Last-minute promos active. Book today!

Popular amenities for Spring Hill rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A heated pool sits within a screened enclosure, featuring a clear blue surface that reflects the surrounding greenery. Adjacent to the pool, an outdoor kitchenette is visible, along with multiple seating options for relaxation and enjoying the outdoors.

4.93 out of 5 average rating, 70 reviews

*No Service Fees*"Shore Fun, Bare Feet Retreat"

4.96 out of 5 average rating, 26 reviews

Home in Port Richey

Bahama Behms pool house by the marina

5 out of 5 average rating, 13 reviews

Home in Hernando Beach

NEW/Waterfront/Pool/Outdoor kitchen/ Dock&BoatRamp

4.96 out of 5 average rating, 67 reviews

A light-filled living area features a spacious sectional sofa and a wooden table with a decorative chair. Natural light streams in through large windows with shades, illuminating the neutral color palette and coastal-inspired decor, creating a relaxed environment.

Home in Forest Hills

*NEW* Riverside Retreat w/Pool

5 out of 5 average rating, 10 reviews

An open concept living area features a modern kitchen with blue cabinetry and a large island. A cozy seating arrangement includes a light grey sofa and a decorative rug beneath. Natural light illuminates the space, with a large TV mounted on a blue accent wall.

Home in Hudson

Waterfront 2/2 with a POOL and direct Gulf access

A private pool is set within a spacious outdoor area, featuring inviting blue water and a safety enclosure. Loungers are positioned around the pool, while a shaded patio with a dining table and chairs is visible, providing a pleasant space for outdoor relaxation.

4.88 out of 5 average rating, 92 reviews

Ideal Home in Spring Hill

4.96 out of 5 average rating, 48 reviews

An inviting pool lanai is showcased, featuring comfortable lounge chairs and small tables. An umbrella provides shade, enhancing relaxation by the heated pool. A serene lake view is visible beyond the screened enclosure, surrounded by greenery and residential properties.

Home in Port Richey

LAKEFRONT HOUSE W/ HEATED POOL

A screened-in pool area features a refreshing blue pool surrounded by lounging chairs. A cozy seating arrangement is positioned nearby, complemented by vibrant cushions. Sunlight filters through the mesh ceiling, highlighting the smooth patio surface and the surrounding lush greenery.

4.9 out of 5 average rating, 30 reviews

Misol Oasis Home!

Apartment rentals with a pool

4.96 out of 5 average rating, 23 reviews

The exterior view of a three-story condo building is shown, surrounded by lush greenery. Several parked cars are visible in the foreground, with designated spaces and a well-maintained landscape enhancing the inviting atmosphere of the property.

Apartment in Tampa

MJ’s Condo Minutes from TPA and Busch Gardens

4.83 out of 5 average rating, 6 reviews

A spacious living area features a contemporary sectional sofa, adorned with assorted cushions, positioned beside a glass coffee table. A mounted television is visible on the wall, while large sliding glass doors provide access to the balcony and overlook the community grounds.

Apartment in Tampa

The Urban Oasis – Serene Views!

Apartment in Gulf Island Beach and Tennis Club

A light-filled living area features a comfortable sectional sofa with decorative pillows and a wooden coffee table. Adjacent, a dining space with blue chairs and a kitchen area is visible, providing an open layout that enhances the overall atmosphere.

4.73 out of 5 average rating, 88 reviews

2/2, waterfront, Hudson, private beach, #401

Apartment in Gulf Island Beach and Tennis Club

4.95 out of 5 average rating, 57 reviews

Cozy Gulf Island Resort Condo #603 in Hudson

Apartment in Paradise Lakes

A modern guest room is shown, featuring a spacious bed with neatly arranged bedding. A cozy seating area with a chair and ottoman complements a small desk. A television is mounted on the wall, and sliding glass doors offer views of the outdoor area.

4.92 out of 5 average rating, 24 reviews

Vacation Nude! N5 Studio @ Paradise Lakes

Apartment in Gulf Island Beach and Tennis Club

A boat glides across calm waters during sunset, with two individuals visible. The horizon is adorned with a vibrant orange and yellow sky, reflecting softly on the water's surface. Distant markers dot the serene seascape, enhancing the tranquil atmosphere of the moment.

4.73 out of 5 average rating, 142 reviews

GORGEOUS SUNSETS Starting at $69 night

4.82 out of 5 average rating, 126 reviews

A living room features a comfortable sectional sofa positioned beside a glass coffee table. Natural light enters through large windows, illuminating a cozy reading area with a rocking chair. The walls display a colorful piece of artwork, and a ceiling fan enhances the airy atmosphere.

Apartment in New Tampa

Beautiful and spacious condo centrally located

4.64 out of 5 average rating, 87 reviews

A serene water view is captured, showcasing clear blue skies and lush greenery. The scene features palm trees framing the tranquil water, reflecting a nearby waterfront home and vibrant flowering plants, all creating a peaceful and natural environment.

Apartment in Palm Harbor

Cozy Waterview Condo on the Lake

Other holiday rentals with a pool

The exterior of the home features a welcoming black door with an elegant light fixture on either side. A bright white facade contrasts with dark shutters. A manicured lawn and a large tree provide shade, while a small seating area with two chairs is visible on the porch.

4.94 out of 5 average rating, 31 reviews

Soluna-Fully fenced home with private pool.

5 out of 5 average rating, 46 reviews

A spacious heated pool area is surrounded by a screened enclosure, featuring clear blue water under bright sunlight. A view of the waterfront is visible beyond the pool, with palm trees and homes reflected in the water. Potted plants add a touch of greenery.

Home in Hudson

Beautiful sunsets, waterfront 2/2 pool home

Holiday home in Spring Hill

A heated pool is surrounded by a screened-in area, featuring colorful lounge chairs and an umbrella for shade. A whimsical whale float is seen in the water alongside a potted plant, creating a vibrant space for relaxation and leisure.

5 out of 5 average rating, 69 reviews

Cozy 4-BR W/Heated Pool Near Weeki Wachee Springs

The exterior of the house showcases a two-story structure with a yellow facade and a prominent chimney. A wide staircase leads up to the main entrance, flanked by a spacious deck. Lush greenery surrounds the driveway, which is bordered by a white fence.

4.92 out of 5 average rating, 49 reviews

Weeki Wachee Paradise on Porpoise

A single-story home is presented with a stone-accented facade and a two-car garage. The driveway features patterned pavers leading to the entrance. Lush greenery and palm trees frame the property under a partly cloudy sky.

4.79 out of 5 average rating, 24 reviews

J&M Chic Abode w/Heated Pool

An outdoor pool area features a clear blue pool surrounded by a spacious patio. Colorful chairs are arranged near the pool under a screened enclosure, providing a view of the home’s exterior. Mature trees line the area, enhancing the serene atmosphere.

4.95 out of 5 average rating, 22 reviews

Enjoy the FL weather and heated pool

4.9 out of 5 average rating, 10 reviews

A sparkling swimming pool features vibrant pool floats and is bordered by palm trees. The tranquil canal is visible, with sunset hues reflecting on the water. The outdoor area includes lounge chairs and a dock, creating an inviting space for relaxation and enjoyment.

Home in Hernando Beach

The Salty Mangrove | Pool • Dock • Kayaks

A modern living area features four sleek black lounge chairs arranged around a circular glass table. A textured rug lies beneath them, and large windows are dressed with sheer white curtains, allowing ample natural light to brighten the space.