
Vacation rentals with a pool in Wesley Chapel
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Wesley Chapel
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Millers, BeOne Naturally Clothing Optional Premium
NO PETS OWNER HAS SEVERE ALLERY 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. Clubhouse 2 Swimming Pools, Hot Tub, events like Karaoke, Live Bands and more (fees vary by days of week)

Entire House with Game Room in Lutz - near Tampa
Entire house with a Game Room equipped with a pool table and a foosball table. Designated working area in Master Bedroom. One King Bed, one Queen Bed and two Twin Beds to accommodate a group of up to six people. A TV in each bedroom, living room and game room. Easy access to USF, Busch Gardens, restaurants, malls and beaches. Short distance to Tampa Premium Outlets and Advent Health Center Ice. Playground, Community Pool, Basketball and Tennis Courts are conveniently located across the street.

🌟Historic 1924💕Carriage House🏡Quaint & Cozy☀️🪂
Step into history with this 600 sq ft Carriage House, located in the heart of Zephyrhills’ Historic District. Built in 1924, the main house is lovingly lived in by the owners, while the Carriage House offers guests a private and unique stay on the same estate. 🌟 Prime Location: 2-minute stroll to Downtown Zephyrhills 8 minutes to Skydive City Z-Hills 15 minutes to Hillsborough River State Park Whether for adventure, history, or relaxation, this enchanting retreat makes exploring a breeze.

Poolside Paradise Retreat-spacious 4 bedroom home!
Welcome to The Poolside Retreat! Bring the family, unwind, & have fun at our modern Tampa home, located just a short distance away from beautiful downtown Tampa and other local attractions. If you are looking for a spacious place to stay that incorporates the perfect mix of indoor and outdoor fun, look no further. 4 bedrooms to accommodate 8 guests with fully stocked kitchen and outdoor bar/grilling area. Outside you will find a pool (heated during winter), outdoor seating and covered patio.

Colorful, Comfy Townhome - Community Swimming Pool
Townhome in the heart of Carrollwood/Northdale with all the comforts of home. 1,136 sq ft. Updated everything, including black matte GE Appliances & fully stocked kitchen. Close to countless restaurants, shopping & easy commute to interstates & expressways. Large, community swimming pool. Come As You Are, I try to provide anything you may need for your stay! 9.5 miles-Ray Jay 10 miles-USF 14 miles-Tampa International Airport 15 miles-Downtown Tampa 16 miles-Ybor 36 miles-Clearwater Beach

PondView/Pool/Pickleball/Dryer/Washer/Ground Floor
Pond View ground floor Condo located in within minutes of Tampa Bay's main attractions: Bush Gardens, Hard Rock Cafe and Casino, Tampa Aquarium, Top Golf, Ybor City, Convention Center, I FLY and shopping malls. Condo has a large Resort Style pool, Keyless entry, washer/dryer in the unit and owner on site for if needed. Pickleball, Tennis court, Volleyball, Disc Golf and 24/7 Gym also available. Relaxing community with several ponds and trails to be explored near the unit. FUN/SUN/Business

Heated & Screened in Pool/Coffee Bar/Fully Stocked
🏡 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.

Beautiful and spacious condo centrally located
As proven by the many reviews, we take cleanliness very seriously. To further insure the cleanliness of the property, we thoroughly disinfect frequently used areas such as: Doorknobs, switches, handles, bedside tables, bathroom sinks, toilets, counters, TV remotes, and thermostat. Condo is walking distance to shopping, food, and entertainment. Within minutes to beaches, Moffit, VA hospital, USF, downtown, Ybor, Malls, Bush Gardens, Zoo, Museums, and more. Orlando is within an hour drive.

Lakefront Retreat w/Pool-Views-Elegant Furnishings
Private UPSTAIRS GUEST SUITE comfortably accommodates 3 guests. Features an elegant bedroom, a combo bedroom/entertainment room with kitchenette; plus a full bath & work station. Enjoy a beverage overlooking the nature preserve; relax and swim in the pool. Located just north of Tampa, midway between Orlando & the Gulf Beaches. Just minutes by car to I-75, I-275, outlet mall, ice hockey complex & restaurants. 7 miles to USF/Moffitt/Busch Gardens; 20 to Airport; 30 to Beaches; 60 to Disney.

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.

Red Comfort Trip Private Jacuzzi, near Busch Gard
Welcome to Red Comfort Trip – Private Jacuzzi & Pool near Busch Gardens. This cozy and fully private guest suite offers your own entrance, a comfortable bedroom, living area, full bathroom, and a private patio where you can relax after a busy day in Tampa. You’ll also enjoy a private jacuzzi and access to a large shared pool, all in a quiet residential area just a few minutes’ drive from Busch Gardens, the Hard Rock Casino, and other main attractions.

Hickory Breeze Guest House
We invite you to come and enjoy our little piece of country in north Pasco County, Florida! Not fancy, but comfortable is our objective for our guests! We are not a business (nor are we owned by a business) therefore we do not conduct our hospitality like a business, but rather as hosts looking to meet and make new friends! We do all our own cleaning and set-up in the guesthouse so that we know it is done the way we would do it for our own family.
Popular amenities for Wesley Chapel rentals with a pool
House rentals with a pool

The Jungalow SOHO - Pool/Hot Tub

Family Friendly Oasis Heated POOL - Ace Location

Entire house in Tampa w/ Heated POOL!

Stunning Heated Pool House Close to Tampa & Casino

Spacious home / 35 Foot Pool/Patio on park

The Palm Haus • Heated Pool • Near Beach • Games

Heated Salt Pool & Spa | Near Airport & Downtown

Mediterranean Oasis! Pool, Putt Putt, & Grill!
Condo rentals with a pool

Spacious 2/2 ResortStyle Condo near Downtown Tampa

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

Waterfront Condo - Sunset View of Tampa Bay

Ocean Breeze • Easy - Heated Pool Access

Royal Orleans at Redington Beach ( Studio )

Lovely Condo minutes from beach & King bed

Spectacular beach to bay views from this resort.

Modern Waterfront Condo - Captivating Sunset Views
Other vacation rentals with a pool

Allison Palms Luxury Tampa Townhome + Pool

15 minutes from Snowcat Ridge 2 bed 1 bath barndo

Stay in our Bright and Beautiful Mirada Home

Cozy Townhome| Moffitt| Pool| Gym| Fast WiFi| 2B2B

"High-End Big, Bold & Beautiful.

Poolside Tiny Guesthouse – Palm Oasis

3BR Condo Pool & Hot Tub • Gym • Central location!

Lakehills Paradise Modern Home with heated pool
When is the best time to visit Wesley Chapel?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $211 CAD | $226 CAD | $225 CAD | $220 CAD | $201 CAD | $203 CAD | $252 CAD | $214 CAD | $196 CAD | $235 CAD | $281 CAD | $276 CAD |
| Avg. temp | 17 °C | 18 °C | 20 °C | 23 °C | 26 °C | 28 °C | 29 °C | 29 °C | 28 °C | 25 °C | 21 °C | 18 °C |
Quick stats about vacation rentals with a pool in Wesley Chapel

Total vacation rentals
Explore 170 vacation rentals in Wesley Chapel

Nightly prices starting at
Wesley Chapel vacation rentals start at $55 CAD per night before taxes and fees

Verified guest reviews
Over 1,610 verified reviews to help you choose

Family-friendly vacation rentals
90 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 110 rentals that welcome pets

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wifi availability
160 of Wesley Chapel vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Wesley Chapel rentals

4.7 Average rating
Wesley Chapel stays receive an average rating of 4.7 out of 5 from guests
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- Walt Disney World Resort Golf
- Disney Springs
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Magic Kingdom Park
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- John's Pass
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
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- Amalie Arena
- Disney's Hollywood Studios
- Island H2O Live!
- Jannus Live
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- ZooTampa at Lowry Park
- Hard Rock Casino
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