Vacation rentals with a pool in Leesburg

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Top-rated rentals with a pool in Leesburg

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

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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$20,976 GYD per night

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$29,868 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.

Oct 9 – 16

G$19,006 GYD per night

Guest favorite

Home in Mount Dora

4.94 out of 5 average rating, 109 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!

Aug 25 – Sep 1

G$33,471 GYD per night

Guest favorite

Guest suite in Leesburg

4.89 out of 5 average rating, 55 reviews

Mid Century Living on Lake Eustis. Dock available.

Great location for Sport Fishing! Unique apartment attached to a Mid Century home located on Lake Eustis. Docking for boat available. Includes Queen size bed, Kitchenette with original Mid Century cabinets. Vintage mini-fridge/freezer, electric range and Microwave, Keurig, Toaster. BBQ. HDTV has 75 AIR channels. Walk in closet for clothes and storage. sit on the dockand watch the local wildlife, or cast a line fish. Pool is not heated. We have changed our policy to a maximum 2 week stay.

Feb 10 – 17

G$18,505 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 22 – 29

G$22,109 GYD per night

Guest favorite

Home in The Villages

4.92 out of 5 average rating, 12 reviews

Sunsets and Sawgrass

Welcome to the Fun! Kick back and relax in this calm, stylish, dog friendly space. Located in the southern village of Lake Denham close to Sawgrass for a wonderful meal, nightly concert or a round of championship golf at Southern Oaks. Enjoy the amenities at a Mickeylee Pitch and Putt, Franklin, Homestead, or Ezell Rec Center. Pickleball, Pool, Pool Tables, Bocce Ball, Tennis. So many adventures await. Our space is well appointed with a screened porch and an open inviting floor plan.

Jun 29 – Jul 6

G$30,596 GYD 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

G$19,791 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.

Oct 9 – 16

G$26,333 GYD per night

Guest favorite

Guesthouse in Mount Dora

4.9 out of 5 average rating, 705 reviews

Key West cottage of Mt Dora

Cozy little cottage located in the gardens of the main house. It has a full kitchen. 1 bath with a jacuzzi tub.. Queen size bed and a couch for a 3rd person. THE LOCATION is 3 MILES between Mount Dora ,Tavares & Eustis a short drive or bike ride to all location. I’m 2.5 blocks off Lake Shore Dr. to beautiful Lake Dora. FRESH eggs from the Easter egg hens for your use ( When available) The eggs they lay are pink, green and blue. They will need to be washed before use..

Apr 28 – May 5

G$28,437 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 1 – 8

G$20,023 GYD per night

Guest favorite

Home in The Villages

4.99 out of 5 average rating, 110 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.

Nov 1 – 8

G$31,183 GYD per night