
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.

The Lakeside Cottage
Welcome to The Lakeside Cottage, our home away from home, and a special place we’re grateful to share. Tucked away in a quiet setting, this cozy retreat is perfect for relaxing, reconnecting, and making memories. With 4 bedrooms and 3 bathrooms (including two primary bedrooms), it blends comfort and convenience. Enjoy your own private oasis with lakeside views, private pool & hot tub. Close to shopping, dining, and highways, it’s an easy stay, whether you’re here to explore or simply exhale.

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.

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.

Designers Villa @ Saddlebrook
A Beautiful completely remodeled 3 bedroom 3 bathroom villa with pool, in the prestigious 24 hr guard gated community of Saddlebrook Resort in Wesley Chapel FL. Surrounded with mature landscaping, the community boast 2 of Florida's most Picturesque Arnold Palmer Golf Courses & 45 tennis courts. Everything you need for a great stay is here! Tons of area restaurants as well as onsite! Everything is NEW, TV in every room, printer, fireplace & more! You will absolutely love it here!! See you soon!

Leithen Lodge Is Like a Scottish Castle in N Tampa
Leithen Lodge is a gated lakeside Gem awaiting your luxury visit. Private pool & spa heated for add’l charge of $100per day spa only, $35 per day, wood burning fireplace, gourmet kitchen & fantasy master suite. Paradise Lakes is a CLOTHING OPTIONAL resort. North of Tampa but within drive of beaches, outlet malls Busch Gardens trendy Seminole Heights Tarpon Springs and countless outdoor and nature adventures. Be King or Queen of your own Castle as you enjoy your own Game of Thrones Fantasy...

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.

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.

Lakeview Retreat with Private Pool Perfect Getaway
Welcome to our charming Tampa retreat! This newly renovated house has been carefully designed with an open layout, it features 2 bedrooms and 2 full bathrooms. The highlight of this home is undoubtedly the patio area, beautiful outdoor furniture, and an amazing pool with a stunning and unique view of the lake canal. The location is perfect, everything is nearby with quick access to major highways such as I-4, I-75, and I-275.

Ranch Pool Resort with Horses jacuzzi nearby park
Take it easy at this unique and tranquil getaway. This is a country setting close to the city of tampa bay on 6 acres gated with every detail in mind Owner maintained ranch style property with 4 horses you will feel at home away from your home trees surround the outer perimeter as well as a huge pool with layout chairs. Take a stroll through the nature walk trail. Experience nature in luxury at this beautiful ranch home!

Stilt House & Pool
Experience an authentic Florida Stilt House stay with curated comforts & amenities. Transform market finds into fresh meals in the full kitchen. Reset with nostalgic board games, books, & movie nights as you tuck in after a day of adventure. The treehouse style wrap around porch & the pool loungers invite you to linger. EV charging available (message for details) + Starlink + Roku.
Popular amenities for Wesley Chapel rentals with a pool
House rentals with a pool

“Sunny Retreat”Pool & Mini Golf

Relax & Explore in a Private heated pool - hot tub

Tampa's Hidden Gem 5/ 2.5 pool/Game-Theatre room !

Lake Townhome w/ Pool near USF, Busch Gardens

Tampa Luxe Oasis Pool, Spa & Games 14 Guests

3/2, 3 miles to Busch Gar *Pool, Game,CoffeeBar*

Saltwater Pool • Kayaks • Pedal boat + more!

Luxe Retreat•Private Pool•4 Miles to Busch Gardens
Condo rentals with a pool

Lovely Waterview Condo/ heated pool

Tiki Themed Waterfront Condo on Tampa Bay

Tampa Bay Waterfront Views Rocky Point

Rocky Point paradise

Beach Front Madeira Beach

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Beautiful and spacious condo centrally located

Florida Breeze
Other vacation rentals with a pool

Pool, Heated Spa Paradise in the City/King bed

“A little Piece of Paradise” beautiful condo

Luxury getaway, Heated Pool, Weeki Wachee

Allison Palms Luxury Tampa Townhome + Pool

Boho Boutique • Balcony Swing Chair • Pool • Gym

Getaway entire house in Wesley Chapel/ Tampa

Welcome to Our Charming Tiny Home in Zephyrhills

Luxury rural-farm stay-pool-farm animals-private
When is the best time to visit Wesley Chapel?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $282 CAD | $245 CAD | $325 CAD | $221 CAD | $202 CAD | $205 CAD | $254 CAD | $216 CAD | $198 CAD | $237 CAD | $283 CAD | $278 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 1,890 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wifi availability
170 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
- Walt Disney World Resort Golf
- Disney Springs
- Raymond James Stadium
- Magic Kingdom Park
- Busch Gardens Tampa Bay
- Epcot
- Disney's Animal Kingdom Theme Park
- John's Pass
- Old Town
- Weeki Wachee Springs
- Reunion Resort Golf Courses - Palmer & Watson
- Vinoy Park
- Amalie Arena
- Tampa Convention Center
- Dunedin Beach
- Disney's Hollywood Studios
- Sand Key Beach
- Island H2O Live!
- Southern Dunes Golf and Country Club
- St Pete Beach
- ChampionsGate Golf Club
- Hard Rock Casino
- Jannus Live





