Holiday 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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Guest favourite

Home in The villages Florida

4.97 out of 5 average rating, 207 reviews

The Village’s Coffee or cocktails on the course !

EXCELLENT ROBUST WI FI FOR THE ENTIRE PROPERTY . CHECK OUT TIME IS 10AM Wake up with Coffee or afternoon cocktails on the fifth hole of the Tierra Del Sol Country Club close to Spanish Springs and Lake Sumter Landing town squares. In the Village of Santiago. Free live music 365 days at each of three town squares. CLose to shopping, golf and pools. Enjoy day of golf, swimming, a country club dinner and dancing on the square NO smoking environment. NO children Also, no pets allowed.

Guest favourite

Home in Lady Lake

4.96 out of 5 average rating, 284 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.

Guest favourite

Guesthouse in Leesburg

4.97 out of 5 average rating, 355 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

Guest favourite

Home in The Villages

4.95 out of 5 average rating, 118 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!

Guest favourite

Home in The Villages

4.94 out of 5 average rating, 124 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!

Guest favourite

Place to stay in The Villages

5 out of 5 average rating, 54 reviews

Safari themed private addition with pool/hot tub.

This special Guest house addition is close to everything in The Villages! Making it easy to plan your visit.! We are in The Village of Osceola Hills at Soaring Eagle Preserve. A short golf cart or car ride to Brownwood Square and Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Access to play over 50 golf courses at a minimal fee. Ask us about our easy 4 seater Golf-cart rental and upon request free Guest passes!

Guest favourite

Home in The Villages

4.92 out of 5 average rating, 135 reviews

Briar Meadow Villa

Dogs are welcome in this nicely furnished Courtyard Villa, with a fenced in backyard. Near Nancy Lopez Legacy Golf & Country Club, Mulberry Grove Rec Center, dog park, Publix, Walgreens, & The Club Health & Rehab Clinic. Easy access to pools, golf courses, dining, shopping & the squares at Spanish Springs & Sumter Landing. Access to The Villages amenities available for a $50 fee payable to The Villages. Golf Cart, Comcast cable TV, high speed WIFI, & Villages Daily Sun included.

Guest favourite

Villa in Lady Lake

5 out of 5 average rating, 5 reviews

Heart of The Villages

Stunning villa in The Villages! Whether you're looking for a peaceful retreat or an action-packed vacation, this home has it all. Enjoy breathtaking sunsets and serene water views from the patio and both bedrooms. The spacious open floor plan features a 65" TV and newer furniture, creating the perfect space for unwinding after a day of adventure. Near Sumter Landing and Spanish Springs, easy access to all the amenities and activities that The Villages has to offer.

Guest favourite

Home in The Villages

4.99 out of 5 average rating, 125 reviews

Whole House 3 Bedroom (sleeps 10) in The Villages

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.

Guest favourite

Home in Wildwood

4.97 out of 5 average rating, 58 reviews

New home in the new part of the villages.

Beautiful new home in the villages. All new appliances with all brand new furniture, beds and decor. You have quick access to Sawgrass grove Entertainment facility, Ezell recreation center and McGradys pub. This open floor plan with the kitchen opening to living room keeps everyone together. The huge island is a great hanging out spot. You will have access to many close by, pools, shuffle board, parks and golf courses during your stay.

Guest favourite

Home in The Villages

4.94 out of 5 average rating, 102 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

Guest favourite

Home in The Villages

4.96 out of 5 average rating, 70 reviews

3 BR 2 BA Coastal-vibe,Golf Cart,Pools, Pickleball

URBAN SÓL Vacation Home You’ll love this costal-vibe home located between Spanish Springs & Lake Sumter Landing in The Villages. This 3 bedroom | 2 bath home comes completely furnished with modern amenities to accommodate your vacation needs! Enjoy the use of our 4 passenger golf cart to explore The Villages. There’s so much to do and see! This vacation rental is perfect for longer stays, business trips, or getaways!