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Vacation rentals with a pool in Wildwood

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Wildwood

  • Total vacation rentals

    Explore 470 vacation rentals in Wildwood

  • Nightly prices starting at

    Wildwood vacation rentals start at €35 per night before taxes and fees

  • Verified guest reviews

    Over 9,030 verified reviews to help you choose

  • Family-friendly vacation rentals

    420 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 150 rentals that welcome pets

  • Rentals with dedicated workspaces

    260 properties have a dedicated workspace

  • Wi-Fi availability

    470 of Wildwood vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wildwood rentals

  • 4.9 Average rating

    Wildwood stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated rentals with a pool in Wildwood

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost
A modern living area features a spacious sectional sofa in gray, complemented by a wooden coffee table. The open floor plan connects to a kitchen with stainless steel appliances and seating for four at the bar. Decorative wall elements add interest to the neutral walls.
Home in Lake Panasoffkee

Heated Pool & Kayaking House in Lake Panasoffkee

Bring the whole family to this great place with lots of room for fun. Enjoy this stylish house very close to the lake. Create new memories while staying at this beautiful property and all its amenities such as an indoor pool with nature view. Designed play room with pool/hockey air table and so much fun. With lake access from the its yard and 5 minutes from all restaurants and entertainments at Lake Panasoffkee. This fully renovated house will make your trip a unique and unforgettable experience

4.85 out of 5 average rating, 117 reviews
Top guest favorite
An inviting outdoor space features a spacious in-ground pool with a sunken hot tub nearby. The pool area is enclosed by a screened lanai, allowing for privacy. Light reflections dance on the water's surface, creating a peaceful ambiance.
Place to stay in The Villages

Safari themed private addition with pool/hot tub.

This special Guest house addition is Central to everything in The Villages! Making it easy to plan your visit. In The Village of Osceola Hills @ Soaring Eagle Preserve. Just North of Rt 44. A short golf cart or car ride to Brownwood Square & Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Play over 50 golf courses at a minimal fee, & free rec centers! We have an easy 4 seater Golf-cart rental , & request free Guest passes!

5.0 out of 5 average rating, 128 reviews
Guest favorite
A single-story home is situated on a corner lot, surrounded by well-maintained lawns and landscaping. Large trees provide shade, while the blue sky creates a bright backdrop. A screened-in porch and patio area are visible on the side of the house.
Home in The Villages

Whole House-sleeps 10 The Villages Spanish Springs

Live Music on the Square. Golf, Pools, tennis, etc. Entire house in the Village of Del Mar located within the exclusive gated community of The Villages, Florida! A three-bedroom, two-bathroom spacious home with a living room with a sleeper sofa, dining room, lanai and a patio with a grill. It is located on a corner lot, only an 8-minute walk (2 minutes by car or golf cart) to Spanish Springs Town Square and a short distance to three different executive golf courses and dozens of amenities.

4.98 out of 5 average rating, 163 reviews
Top guest favorite
An elegantly appointed dining area is highlighted by a dark table surrounded by gray upholstered chairs. Two candles sit atop the table, with a decorative bowl in the center. Soft lights hang overhead, illuminating the blue walls adorned with framed art and decorative shelves.
Villa in The Villages

Perfect "get-away" home for a couple or family!

Great getaway for a single, couple, or a family. Only an hour from the Disney Parks! By golf cart, you are only minutes from pools, rec. centers, golf courses and many dining options as well as the grocery store. The home includes a nice outdoor seating area. The "squares" provide FREE nightly entertainment. Golf cart included in price for getting around in The Villages. This get-away home is perfect for people looking to relax OR never be bored! It's always a great day at The Villages!

4.86 out of 5 average rating, 278 reviews
Top guest favorite
An extended lanai features a dining table surrounded by cushioned chairs, with views of a heated saltwater pool and lush greenery beyond. Comfortable seating arrangements are designed for relaxation, while ceiling fans provide a gentle breeze throughout the open space.
Home in The Villages

New Luxury Home-Pool-Waterfront View-3 King Suites

Enjoy this unique, tranquil getaway in a new 2023 home less than 3 miles from Sawgrass Grove (nightly entertainment, restaurants), and only a few blocks from Mickylee Pitch and Putt, Jubilee Putting Course, and the new Franklin Recreation Center. Ezell, Homestead, and Citrus Grove Rec Centers are all under 3 miles away. Back yard with lanai, pool with fountain, pond, and trees is a RARE find in The Villages! 3 king bedroom suites! Golf cart (4 seats) available for an additional fee.

4.98 out of 5 average rating, 115 reviews
Top guest favorite
Home in Wildwood

Newest Hotspot in The Villages Eastport/Middleton”

Welcome to Eastport! The Villages’ most exciting new lifestyle destination — Eastport! Whether you're visiting for a weekend getaway or an extended stay, this beautifully furnished 2-bedroom, 2-bath Patio Villa w/golf cart puts you in the heart of everything The Villages has to offer — golf, pickleball, shopping, dining, entertainment, recreation, and serene nature. From the moment you arrive, you’ll see why Eastport is the new standard for luxury, leisure, and active adult living.

5.0 out of 5 average rating, 42 reviews
Superhost
An exterior view of the patio villa showcasing a well-maintained façade. A garage door is located to the left, with a Yamaha gas golf cart parked on the driveway. A white picket fence and colorful flowers enhance the entrance.
Villa in The Villages

Location Can’t be Beat! With cart!

Experience The Village's retirement community lifestyle! The patio villa is located near Spanish Springs Town Square and the shopping corridor, where you will find nightly entertainment, dining and shopping. Walk to Savannah Center & Glenview Country Club. Your rental includes the complimentary use of a Yamaha gas golf cart and Guest ID cards that provide you access to our recreation facilities. Monthly guests may purchase Resident ID cards ($50) that include free executive golf.

4.84 out of 5 average rating, 134 reviews
Top guest favorite
The image captures a welcoming street view of a residential area with charming homes featuring varied architectural styles. Lush palm trees and neatly trimmed shrubs outline the landscaped front yards. The sky is bright with fluffy clouds, contributing to the overall inviting atmosphere.
Home in The Villages

1199 Merryweather - Walk to Lake Sumter Sq 3nt min

Wow! Gorgeous 2br/2ba courtyard villa w/5-star reviews. Walk to Creekside Landing pool & town square in THE most sought after location in the community. Private yard. Granite counters, vaulted ceilings, big birdcage, French doors & vinyl plank floor. No carpet. Nice recliners, patio chairs, and sofa. King in master br. Queen in guest br. Cable. WIFI. Rent a golf cart (optional). No pets here. I manage a pet friendly 3br across street (sleeps 6). Rest of 2026 is just a 3nt min.

4.94 out of 5 average rating, 103 reviews
Top guest favorite
Home in The Villages

King Bed, Golf Cart, Small Dogs & Water Filter!

Your NEW home includes a very comfortable KING BED and GOLF CART!! With its SUPER CLEAN coastal decor, fully equipped kitchen for meal prep, and a whole house NOVA WATER filtration system, you’ll have everything you need for a relaxing and enjoyable stay in The Villages. Find out why The Villages is the fastest growing and largest 55+ community in the WORLD, where visitors of all ages are welcome to play. The fun and sun is only the beginning!! 2 SMALL DOGS OK.

4.96 out of 5 average rating, 105 reviews
Top guest favorite
Cottage in Clermont

Private Country House | 16 Guests | Gatherings

Bring the whole family to this private 5-acre retreat, situated in one of the few hilly regions of Florida. Enjoy privacy, nature, spectacular sunsets, and starry nights—perfect for relaxing or enjoying outdoor activities. ⚠️ Gatherings require prior approval—please contact us before booking. Note: There is another house on the property that may be rented by other guests. Both are completely private, with no shared areas or parking.

4.93 out of 5 average rating, 149 reviews
Guest favorite
Home in The Villages

Htd Pool & Attached Hot Tub. Rare corner propty

New heated pool with attached hot tub and waterfall! Located in the coveted Village of Richmond, experience a rare rental retreat with stunning 270° water views and total privacy near Brownwood Square—minutes from shopping, dining, and medical facilities. Enjoy a breathtaking bird estuary sanctuary while relaxing in the new heated pool with attached hot tub, open-concept living with elegant finishes, and a fenced backyard oasis.

5.0 out of 5 average rating, 6 reviews
Guest favorite
An enclosed patio features a heated saltwater pool, accentuated by stone tile and decorative mosaic. Nearby seating options are visible, including a lounge chair under a shaded canopy. Lush greenery surrounds the area, providing a sense of privacy and tranquility.
Home in The Villages

Villages-Private Heated Pool-Central Location

Enjoy a stylish experience at this centrally located 3-bedroom home. 5-7 minutes golf cart ride from Sumter Landing, 15 minutes from Spanish Springs Square, 20 minutes from Brownsville Square. 200 Community pools some for adults only and some for families. 13 Recreation Centers with Pickle Ball, Shuffleboard, Billiards, Study groups, etc. 3 Old Fashion Town Squares with nightly Live entertainment. 44 Golf Courses

4.94 out of 5 average rating, 162 reviews

Popular amenities for Wildwood rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favorite
A well-maintained exterior of a single-story home is presented, featuring a light yellow facade and a welcoming front porch. Lush greenery and palm trees are positioned along the pathway, with a manicured lawn and trimmed shrubbery enhancing the curb appeal.
Home in The Villages

2/2 custom pool home with 4 person gas golf cart

4.96 out of 5 average rating, 156 reviews
Top guest favorite
A sun-drenched pool area features a sparkling blue pool surrounded by comfortable seating. A table with an umbrella and colorful chairs offer space for relaxation. The sunroom with large windows provides views of the inviting outdoor space, enhancing the overall tranquil setting.
Home in Lady Lake

Cozy Lady Lake Guest House

4.96 out of 5 average rating, 355 reviews
Guest favorite
A private heated pool is framed by a spacious lanai with a sleek, white deck. The pool features a shimmering blue surface and tiled border. Surrounding walls provide privacy while natural light pours in from above, creating a bright and inviting space.
Home in Wildwood

New, private pool getaway in The Villages, FL

4.91 out of 5 average rating, 99 reviews
Top guest favorite
Home in The Villages

Pool House Near Eastport and Middleton

5.0 out of 5 average rating, 30 reviews
Guest favorite
A wooden boardwalk winds gracefully along the edge of a tranquil waterway, surrounded by lush greenery and mature trees. Nearby, a pavilion stands, offering shaded views of the serene landscape, enhancing the outdoor experience.
Home in Wildwood

StJohns is a great area for golf, hiking, Kayaking

4.96 out of 5 average rating, 23 reviews
Top guest favorite
A heated saltwater pool is highlighted under a screened enclosure, with ambient lighting creating a calming atmosphere. Patio seating is arranged around the pool, and views of the adjacent living area are visible through expansive windows, enhancing the inviting indoor-outdoor connection.
Home in The Villages

Pirates & Parrots - The Villages - Golf Cart &Pool

5.0 out of 5 average rating, 61 reviews
Top guest favorite
Home in Wildwood

Stylish Villages Getaway

5.0 out of 5 average rating, 12 reviews
Top guest favorite
A screened-in patio features a refreshing private pool surrounded by lush landscaping. Two chaise lounges are positioned beside the water, while a float rests in the pool. A fountain adds a tranquil element to the relaxing outdoor space.
Home in The Villages

Casa Santin Luxury in The Villages w/Private Pool

4.97 out of 5 average rating, 97 reviews

Condo rentals with a pool

Guest favorite
Condo in Orlando

Cozy space 5/10 universal & epic

4.84 out of 5 average rating, 159 reviews
Top guest favorite
An aerial view of the clubhouse area is displayed, featuring a large pool surrounded by lounge chairs. Palm trees provide greenery around the poolside, while guests can be seen enjoying the water. The architecture of the clubhouse complements the inviting outdoor space.
Condo in Orlando

Location,Location 3bd 2bth near parks conv.ct/Int.

4.93 out of 5 average rating, 160 reviews
Top guest favorite
Condo in Orlando

IS1-107 - 2BR condominium near Disney

4.95 out of 5 average rating, 127 reviews
Top guest favorite
A vibrant living area features a Super Mario-themed mural depicting iconic characters against a blue backdrop. Plush seating surrounds a coffee table styled with bright colors, while a playful rug showcases a character from the Mario universe, creating a fun and inviting atmosphere for relaxation and gaming.
Condo in Orlando

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

4.95 out of 5 average rating, 194 reviews
Guest favorite
Condo in Orlando

Modern Lake view Condo 1 mile from Disney

4.95 out of 5 average rating, 139 reviews
Guest favorite
A spacious outdoor area features several palm trees and seating arrangements with turquoise cushions. The backdrop includes a modern multi-story building. A barbecue area is visible, and lounge chairs are positioned around a sparkling pool, creating an inviting environment for relaxation.
Condo in Orlando

Luxury Condo On I-Drive & One Mile from Universal

4.87 out of 5 average rating, 147 reviews
Top guest favorite
A balcony view captures a vibrant sunset over Lake Bryan, with hues of pink and orange reflected on the water. Outdoor seating includes two chairs and a small round table, inviting relaxation while enjoying the scenic surroundings.
Condo in Orlando

Lakefront Resort Condo near Disney and Universal

4.98 out of 5 average rating, 264 reviews
Guest favorite
Condo in Orlando

Recently Updated: 3b2b, Lake, Pool, Shuttle, Gym!

4.92 out of 5 average rating, 204 reviews

Other vacation rentals with a pool

Top guest favorite
The exterior of a single-story home is showcased, featuring a well-maintained front yard with greens and flowering shrubs. A paved driveway leads to a two-car garage, while the entrance is framed by neat landscaping. The sky above is clear and bright.
Home in The Villages

The Villages, Citrus Grove home away from home

4.96 out of 5 average rating, 24 reviews
Guest favorite
A golf cart is parked on a driveway leading to a home. Tropical plants and palm trees create a lush exterior atmosphere. The garage door is visible on the right, with a sunny sky and scattered clouds overhead.
Home in The Villages

Holiday home in the villages.

4.82 out of 5 average rating, 66 reviews
Guest favorite
A spacious home is showcased amidst lush landscaping, featuring multiple palm trees and colorful shrubs. The exterior highlights a warm yellow facade with a welcoming front porch. A clear blue sky with scattered clouds adds to the inviting atmosphere of the property.
Home in The Villages

The Grandview

4.76 out of 5 average rating, 38 reviews
Top guest favorite
The kitchen features modern stainless steel appliances and a large island with seating for four. The quartz countertops complement the rich cabinetry and vibrant blue wall. Pendant lights provide illumination, enhancing the sleek design of the space.
Home in The Villages

Designer Home in The Villages, FL.

5.0 out of 5 average rating, 27 reviews
Top guest favorite
A stylish villa exterior is presented with a gray facade and a welcoming porch area. A well-maintained lawn features a white picket fence and newly planted shrubs. A golf cart is parked on the driveway, ready for use, while the surroundings depict a tranquil neighborhood setting.
Home in Wildwood

Newer Villa in The Villages near Brownwood

4.97 out of 5 average rating, 94 reviews
Top guest favorite
Home in The Villages

Eastport Emerald Escape 2BR Luxury in Well Point

5.0 out of 5 average rating, 22 reviews
Guest favorite
A private outdoor area features a heated pool and spa, surrounded by screen enclosure. Comfortable seating is arranged beside the pool, complemented by an outdoor dining setup. The space is designed for relaxation with a stylish stone paver patio and clear blue skies above.
Home in Wildwood

Pool and Spa Luxury Retreat

4.94 out of 5 average rating, 17 reviews
Superhost
Home in The Villages

The Sunseekers Eco-Villa

4.86 out of 5 average rating, 14 reviews

When is the best time to visit Wildwood?

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Avg. price€156€177€175€130€108€109€98€96€97€103€117€128
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

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