Holiday rentals in Oxford, Wildwood

4.95 out of 5 average rating, 19 reviews

Villages - Heated Pool 3BR/2BA Convenient Loc.

Enjoy our newly updated home and forget your worries in this spacious and serene space. A 3 BR/2BA home with heated pool that sleeps 6 (extra fees over 4.) 3 bdrms w/TV's (King, Queen & Twin beds.) A splendid quiet neighborhood location within The Villages, an active community with many amenities. Close to Sumter Landing, Arnold Palmer Golf course, Churchill Downs executive course, Pimlico Recreation Center (pickle ball, pool, billiards, etc.) Convenient proximity to many stores and restaurants.

4.97 out of 5 average rating, 31 reviews

2/2 Cottage between Sumter/Brownwood Pet Friendly

Want to squeeze the most out of your vacation? This 2 bedroom, 2 bathroom cottage home will steal your heart away in the desirable Village of Buttonwood. You will love the feeling of being on a permanent vacation as you enjoy your morning coffee in the private lanai with wide open kitchen, washer/dryer and vaulted ceilings. Walking distance to the Fishhawk Pool & Rec center and many golf courses. Not to mention equal distance between Lake Sumter Landing & Brownwood Paddock Squares. $75 pet fee.

5 out of 5 average rating, 8 reviews

Lynnhaven | 2 miles Sumter Square | walk to pool

2 miles from Lake Sumter Town Square, 3 blocks to rec center, Southern Oak has everything you need in this newly updated 2 /2 Colony home. A perfect space centrally located between the 6s to explore The Villages. The home features an open concept dining & living area, & enclosed year round patio w/ sitting area. In-unit washer & dryer. WIFI & parking included. Golf cart accessible. Guest passes available upon request (provide info 3 days prior to check-in). Dogs 35 lbs & under w/fee max 2 dogs.

5 out of 5 average rating, 12 reviews

Ensō House Relax in the heart of The Villages

This 3/2 stucco designer home is a block away from Glenview Championship Golf Course and a short golf car ride to Sumter Landing or Spanish Spring town squares. The 1400 sq ft home is fully furnished with modern decor, luxury linens, and 4 person golf car. The backyard’s fully enclosed birdcage has seating for 6 plus 2 sun loungers. King bed in primary, queen in 2nd, and sleeper sofa in 3rd bedroom. Enjoy a fully equipped kitchen, exercise equipment, 4 new smart TV’s, and 2 bicycles in garage.

4.98 out of 5 average rating, 115 reviews

Private 2/2 Villa w/ New 4 Seat Gas Golf Cart

Relaxing home in quiet neighborhood w/ private yard, screened porch - rare in The Villages! Roanoke Retreat is a beautifully remodeled 2 bed/2 bath home - only 15 minute golf cart ride to Spanish Springs, 20 minutes to Sumter Landing . Rental includes 4 seat gas golf cart w/ access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Smart TV's in every room, fully equipped kitchen, new BBQ grill. 55+ community but no age restriction to visit

Superhost

4.92 out of 5 average rating, 13 reviews

Sunnyside Up

This dog friendly 2BR 2BA, in The Village of Belvedere, plus office is your home away from home in the sought after Village of Belvedere. This home is nestled in the heart of the villages, in between Spanish Springs and Sumter Landing located in close proximity to shops, restaurants, bars, night live entertainment, and rec centers. Sunnyside Up has so much to offer. You enjoy time spent on the extended enclosed lanai w/HVAC system or outdoors on your back porch w/enclosed birdcage w/BBQ.

5 out of 5 average rating, 17 reviews

Heated Pool, Dog Friendly, Golf Cart Included

Welcome to your dream getaway! Our exquisite 2 bed, 2 bathroom home is a true haven of luxury and relaxation. From the moment you step through the front door, you'll be enveloped in an atmosphere of opulence. Indulge in a restful night's sleep in our meticulous bedrooms, each adorned with plush bedding and upscale furnishings. The sparkling pool beckons for refreshing swims, while the adjacent hot tub provides the perfect spot for soaking under the stars. Don't forget the games room.

4.88 out of 5 average rating, 16 reviews

The Grandview

Sure to wow and impress you, this stunning premier home has it all. With four spacious bedrooms, you can bring the whole family for some memories and fun. A sparkling pool and an inground hot tub await you on the sprawling lanai, complete with ample seating and an outdoor kitchen. This home is just minutes from Lake Sumter Landing and all the shopping, dining, golf, recreation and activities you could imagine! Golf cart for your convenience. Golf cart is not guaranteed.

4.99 out of 5 average rating, 116 reviews

VIEW-T-FUL! w/Golf cart

Stunning entry with one of a kind picturesque setting and unbeatable location all in one. This lanai was redesigned with no support columns to have this spectacular highly desirable panoramic golf front & water view. Sweeping view of Southern charm, cluster of mature oak trees with Spanish moss. The back of the home facing the morning sunshine lighting up the lanai and screen area for a fine morning of relaxation. Don't hesitate, this home has it all, golf cart too!

4.96 out of 5 average rating, 184 reviews

Home in Ocala

Cozy A-Frame Retreat w/ hot tub!

Escape to our cozy A-frame cabin, nestled amidst the serene beauty of nature. Just 10 mins from Santos Trailhead and 35 from Rainbow Springs! After a day of exploration, unwind in the private hot tub, gather around the bonfire pit for s'mores, or snuggle by the fireplace and stream your favorite movie. Whether you seek a romantic retreat or an extended family getaway, our A-frame cabin promises the perfect blend of nature's tranquility and modern comfort!

4.95 out of 5 average rating, 127 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