Vacation rentals with a pool in Wildwood

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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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Guest favorite

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.

Dec 9 – 16

G$29,855 GYD per night

Guest favorite

Guesthouse in Leesburg

4.98 out of 5 average rating, 333 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.

Oct 16 – 23

G$20,967 GYD per night

Guest favorite

Villa in The Villages

4.87 out of 5 average rating, 71 reviews

Patio Villa Near BrownWood

Enjoy your beautiful Colony Patio Villa in PINELLAS. Near Brownwood Town Square, Eisenhower regional rec center, & Bonifay and Evan’s Prairie CCs. WALKING DISTANCE to Big Cypress, 3 executive courses, and PINELLAS PLAZA (with Winn Dixie, restaurants & more) January to March bookings must be for a full calendar month (beginning and ending on the 1st and last, respectively) The Villages is an Active 55+ Community. Young visitors are allowed for limited periods with plenty of family activities.

Nov 22 – 29

G$24,144 GYD per night

Guest favorite

Home in The Villages

4.98 out of 5 average rating, 50 reviews

LAVISH Private House w/ King Bed Suites, Remodeled

☑ 2 New King bed suites + Queen ☑ Brand new appliances! ☑ Remodeled bathrooms! ☑ Flatscreen TV's ☑ High-speed, Strong Internet. A gorgeous remodeled home in the Village of Duval! New bathrooms with walk-in showers, new appliances, new furniture, and new granite countertops. New king beds, linens, and towels. Imported porcelain tile throughout the house, no carpet. High-speed Internet and large flat screen TVs in all bed rooms plus living room. House is not childproofed. GOLF CART NOT INCLUDED.

Nov 12 – 19

G$33,783 GYD per night

Guest favorite

Home in Lady Lake

4.97 out of 5 average rating, 270 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.

Aug 2 – 9

G$21,126 GYD per night

Guest favorite

Home in The Villages

4.94 out of 5 average rating, 108 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!

Sep 6 – 13

G$36,710 GYD per night

Guest favorite

Home in The Villages

5.0 out of 5 average rating, 10 reviews

The Villages Golf Pickle Pools Music Golf Cart

Discover this delightful home, situated in the heart of a vibrant and lively golfing community with pristine landscaping. From the artsy to the sports enthusiast, there's something here for everyone. 2-person golf cart available for use to be able to fully enjoy the Villages lifestyle! Live music fills the air every night across four inviting outdoor venues, 1 within a 5-minute golf cart ride! With over 100 pools and scenic hiking trails, you can unwind or stay active at your leisure.

Jun 23 – 30

G$19,714 GYD per night

Guest favorite

Home in Wildwood

4.95 out of 5 average rating, 19 reviews

Villa in The Villages Great Location

Kick back and relax in this calm, stylish villa in The Villages. It is in the village of McClure (Fenney area). It is a super clean villa with newer furnishings. The villa comes with a golf cart as a courtesy to enjoy. It is close to Everglades Recreation Center Magnolia Shopping Center, family pools, sports pools, executive golf courses and many other activities. The neighborhood pool is within walking distance to this home! The home is fully furnished and has a fully equipped kitchen.

Sep 19 – 26

G$23,187 GYD per night

Guest favorite

Home in Wildwood

4.93 out of 5 average rating, 29 reviews

*May Rates Reduced 2/2 in Village of Citrus Grove

*Newly Redone* - Brand new furniture throughout - Freshly painted - Screened in Lanai 2 Bedroom, 2 Bath located in Citrus Grove in The Villages, FL Great Location! - Very close to Citrus Grove adult pool - Homestead recreation center with family pool 0.7mi - Ezell Recreation Center 1.1mi - Sawgrass Complex 1.3mi There are several amenities for you to enjoy in The Villages - restaurants, bars, nightly live entertainment, shopping, golf, pickleball, shuffleboard, and so much more!

Jan 20 – 27

G$36,411 GYD per night

Guest favorite

Home in The Villages

4.92 out of 5 average rating, 130 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.

Sep 28 – Oct 5

G$26,185 GYD per night

Superhost

Home in The Villages

5.0 out of 5 average rating, 5 reviews

Patio Villa - Pet Friendly 2/2 Home (South of 44)

**January - March Rentals are Minimum of 60 Days** This is a beautiful FULLY FURNISHED, 2/2 Patio Villa Home . There is a spacious comfy living room with lots of seating as well as TV (cable/wifi) We now offer Golf Cart Rentals for additional fee. (2 Passenger $35/day, $175/week) (4 Passenger $55/day, $275/week) PETS: 2 Small dogs, $60.00. non refund/pet; sec dep will be used for any pet damages; renter liable for entire cost of damage VILLAGE IDs- $25/ea

Jul 18 – 25

G$16,452 GYD per night

Guest favorite

Home in The Villages

4.98 out of 5 average rating, 57 reviews

Home away from home in The Villages

My place is close to family-friendly activities such as community swimming pools and recreation centers and only 45 minutes from Universal Studios and Disney World, nightlife, and three town squares. You’ll love my place because of the location, the people, the neighborhood, the ambiance, and the outdoors space. My place is good for couples and solo adventurers. If you play golf, this is the place for you with many golf courses to choose from.

Oct 5 – 12

G$20,014 GYD per night