Holiday 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 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.

9–16 Dec

₹12,169 per night

Guest favourite

Guest house 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.

16–23 Oct

₹8,537 per night

Guest favourite

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.

31 Aug – 7 Sep

₹9,875 per night

Guest favourite

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.

20–27 Jun

₹13,783 per night

Guest favourite

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.

2–9 Aug

₹8,761 per night

Guest favourite

Villa in The Villages

4.96 out of 5 average rating, 23 reviews

PATIO VILLA W/GOLF CART 1M TO SQ-NO XTRA GUEST FEE

Adorable Patio Villa in a prime location. Located in the heart of The Villages, one mile from Brownwood Town Square - very close to Eisenhower Regional Rec Center, Manatee family pool and Hillsboro adult pool; offering many options for golf, food, and entertainment. Complete with linens, washer/dryer, kitchen equipment, wifi, gas grill, patio furniture screened in lanai, and use of a brand new 4 person golf cart. 2 bedroom, 2 bathrooms with KIng bed in master and twin beds in second bedroom.

23–30 Aug

₹9,051 per night

Guest favourite

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.

9–16 Sep

₹8,058 per night

Guest favourite

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.

28 Jul – 4 Aug

₹9,465 per night

Guest favourite

Home in The Villages

5.0 out of 5 average rating, 7 reviews

Central Villages w/ Golf Cart

Centrally located in The Villages. Use the included golf cart for a short golf cart ride away from 2 Town Squares (Brownwood and Lake Sumter Landing), where there is free nightly entertainment 365 nights/ year. The patio villa is well appointed, including a split-king adjustable bed in the main bedroom, queen bed in the guest bedroom. Tucked away at the end of the street, with a side patio w/ retractable awning and grill. Also screened in lanai w/ blinds. LVP throughout-no carpet.

29 Nov – 6 Dec

₹11,815 per night

Guest favourite

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!

17–24 Jun

₹8,072 per night

Guest favourite

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.

21–28 Sep

₹10,589 per night

Guest favourite

Home in The Villages

4.91 out of 5 average rating, 22 reviews

THE Villages, FL 3/2 Home Pet Friendly Furnished

**January - March Rentals are Minimum of 60 Days** This is a beautiful FULLY FURNISHED, 3/2 home on a Cul-de-sac. There is a spacious comfy living room with lots of seating as well as TV/DVD Player(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

3–10 Aug

₹7,234 per night