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

R2,822 ZAR 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

R1,925 ZAR 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.

Aug 31 – Sep 7

R2,277 ZAR 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.

May 20 – 27

R1,937 ZAR per night

Guest favorite

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.

Aug 23 – 30

R2,050 ZAR per night

Guest favorite

Home in The Villages

4.94 out of 5 average rating, 106 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!

Aug 11 – 18

R3,684 ZAR 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.

Jul 13 – 20

R2,134 ZAR per night

Guest favorite

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.

Nov 29 – Dec 6

R2,661 ZAR per night

Guest favorite

Home in Wildwood

4.93 out of 5 average rating, 28 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!

Jun 16 – 23

R1,833 ZAR 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 21 – 28

R2,381 ZAR 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.

Aug 24 – 31

R1,842 ZAR per night

Guest favorite

Home in The Villages

4.99 out of 5 average rating, 109 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.

Jul 27 – Aug 3

R2,428 ZAR per night