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Vacation rentals with a pool in The Villages

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in The Villages

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

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Home in Ocala

4.8 out of 5 average rating, 103 reviews

Hidden Treasure NE. Pool,Dogs,WEC,SilverSpring SP.

"Hidden Treasure is a comfy family home with 4 bedrooms, two baths, large level yard, parking for vehicles and large built in pool. There is a guest suite on the property that can be booked for an additional fee. parking for large-scale vehicles behind guest house 220x40..room for horse trailers! dogs are allowed with permission and additional fee per dog.50$ per dog, no cats.swim at your own risk. 12 miles to WEC..cameras on home are non functional..guest house can be reserved for 50$per night.

Home in Inverness

4.87 out of 5 average rating, 140 reviews

Zen Spot Sanctuary Heated Salt Water Pool Koi Pond

PRIVACY!!! Bamboo floors bright open & airy. Beautiful furnishings & deluxe bedding. Relaxing quiet & private screened heated pool and deck water toys provided. Large bbq grill with outdoor dining table and chairs. . Spacious yard with Koi pond & sitting/meditation areas. Kayak nearby springs & rivers. Bike, run, walk beautiful Withlacoochee Trail Motor endless Backroads & adventures & explore beautiful nature coast! 2 miles to Historic downtown great restaurants & fun events year round

Home in Lady Lake

4.96 out of 5 average rating, 287 reviews

Cozy Lady Lake Guest House

Private guesthouse in a quiet, rural area of Lady Lake. 1 bedroom, 1 bath, furnished with pool privileges. Kitchen, dining bar, living room and sunroom. Sunroom opens to the pool deck and sparkling blue pool, which is completely privacy-fenced in a common area shared with the owners. Suitable for 1 or 2 adults. Central heat and air, 40” Smart Television , WiFi, washer and dryer. Bed linens and bath towels provided. Kitchen with full sized refrigerator/freezer ice maker and electric stove.

Guesthouse in Leesburg

4.98 out of 5 average rating, 363 reviews

Silver Lake Guest Pool House

The Silver Lake Pool Guest house Is your home away from home 1400 sq feet plenty of room! The pool house is a peaceful place to relax or take a swim in a large salt water pool . Mt Dora Tavares, Eustis 10 to 15 minutes away from Pool house Forty five minutes Daytona, Tampa Smyrna beach and parks Minutes from grocery stores restaurants malls Full kitchen also grilling. We are happy to help you with your needs ! Home is great for couples families, solo adventurers, and business travelers

Home in Inverness

4.97 out of 5 average rating, 108 reviews

Nature Coast Lakeside Getaway- Pool Home w/ Dock

Enjoy lakefront living close to everything the Nature Coast has to offer. Entire home is for your use with a private pool and boat dock. Beautifully decorated and comfortable living space to enjoy some family time. The 3 bedroom home has 2 king beds, 1 bunk bed (twin and full size) and 1 twin trundle bed. Sleeps 8. Enjoy using the 3 kayaks on the lake during the day, then challenge each other to a game of 8 ball at night on the billiards table. Swim and enjoy cocktails by the pool on the lanai.

Home in Mount Dora

4.94 out of 5 average rating, 133 reviews

Modern Farmhouse & Pool in Mount Dora by Lake Ola

This recently renovated farmhouse cottage is the perfect “home away from home” to retreat w/ family & friends. Enjoy waking up to the beautifully updated kitchen w/ farm sink, catching the sunset over Lake Ola while refreshing in the pool, sipping your morning coffee on the large back porch. Only a few minute drive to downtown Mount Dora filled w/renown restaurants & boutiques . Close to Rock & Wekiva Springs, Sydonie Mansion & other wedding venues & easy commute to theme parks and beaches!

Home in The Villages

4.95 out of 5 average rating, 121 reviews

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

Beautiful Monterey style home, 2/2, fully furnished with a heated pool at 85' year round. Great location in Rio Grande; just a short golf cart ride to Spanish Springs & Lake Sumter. Home is on a quiet cul-de-sac; no neighbors behind. Private lanai from the Florida room. Tile and granite countertops throughout; Stainless steel appliances; Sleeper sofa in the LR for extra folks. 4 person gas golf cart. 2 bikes available but not maintained by owner. Sorry, hot tub not included. Pet friendly!

Home in Minneola

4.98 out of 5 average rating, 138 reviews

Spacious Getaway ~ Heated LED Pool & Ping Pong

Welcome to your Spacious Getaway! With over 70 amenities offered, our goal is to provide an unforgettable experience for our guests! Exterior Features: ★ Heated Pool up to 95 Degrees - ($25 a Day to Heat the Pool) ★ LED Lights on pool cage ★ Fenced-in yard & Fire-pit ★ Doorbell & Driveway Camera for safety Interior Features: ★ White/Clean Linens ★ TV with Netflix ★ Ping Pong Table ★ Shower Panel in Guest Bathroom ★Large Shower in Master Bathroom {Willing to Negotiate Monthly Prices}

Home in The Villages

4.94 out of 5 average rating, 127 reviews

Pool, golf cart, private backyard. Paradise!

Come and enjoy this relaxing piece of paradise surrounded by lush greenery with your own, small, private pool (not heated). "Serene on the Green" is a beautifully remodeled 3 bedroom, 2 bathroom designer home (1,536 sqft) with a large screened outdoor pool area with lots of privacy. Our location 320 steps from the Santiago Recreation Complex with two golf courses and a short ride to Lake Sumter Landing and Spanish Springs is perfect. A new custom 2021 Yamaha QuieTech golf cart is included!

Home in The Villages

4.94 out of 5 average rating, 106 reviews

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

Home in Inverness

4.97 out of 5 average rating, 148 reviews

Private 40 Acre Waterfront Retreat on Nature Coast

Welcome to your private oasis; a truly outstanding 40-acre waterfront estate. Experience the exceptional beauty and diverse wildlife that is characteristic of the Nature Coast. Our4400 square foot private vacation retreat invites you to relax by the pool, fish on the river, explore, and take advantage of all the local sites to see. Create special memories reconnecting with nature and each other.

Home in Wildwood

4.96 out of 5 average rating, 110 reviews

Fenney Waterview Retreat w/Pool in The Villages

If you are looking for a Tranquil escape, then this is the right home for you. Sit by the pool and overlook the sun dance upon the sparkling water as you sip on your drink or read a great book. This Ultra Clean 3 bed/3 bath home has all of the comforts you'll be looking for. There's plenty of space for you and friends or family as everyone has their own space in the home.

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Popular amenities for The Villages rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in The Villages

4.89 out of 5 average rating, 44 reviews

3/2 POOL home in The Villages at Polo Ridge.

Home in Inverness

4.94 out of 5 average rating, 32 reviews

Private fenced pool home/dog friendly

Home in Clermont

4.92 out of 5 average rating, 92 reviews

Spacious Bungalow with Private Pool and Courtyard

Home in Ocala

4.94 out of 5 average rating, 80 reviews

Ocala Oasis-3 Bedrooms and Heated Pool!

Home in Ocala

4.83 out of 5 average rating, 29 reviews

Poolside Oasis in Ocala Springs

Home in The Villages

4.92 out of 5 average rating, 138 reviews

Briar Meadow Villa

Home in Ocala

4.97 out of 5 average rating, 72 reviews

Spacious 6BR Pool Home in Ocala

Home in Ocala

4.95 out of 5 average rating, 55 reviews

Screened-in-Heated Pool+Fence+Garage+Arcade+Bbq

Condo rentals with a pool

Condo in Clermont

4.65 out of 5 average rating, 17 reviews

Sunny Clermont Retreat ~ 20 Mi to Disney World!

Condo in Inverness

5 out of 5 average rating, 30 reviews

Gray Heron Victorian Townhouse

Condo in Inverness

4.87 out of 5 average rating, 47 reviews

Cypress Cove Waterfront Townhome

Home rentals with a private pool

Quick stats about vacation rentals with a pool in The Villages

Total rentals
450 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
7.1K reviews
Family-friendly rentals
410 properties are a good fit for families
Pet-friendly rentals
150 properties allow pets
Rentals with dedicated workspaces
200 properties have a dedicated workspace

Destinations to explore