Wildwood vacation rentals

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Top-rated vacation rentals in Wildwood

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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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

G$24,626 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.

Nov 24 – Dec 1

G$18,994 GYD per night

Guest favorite

Home in The Villages

5.0 out of 5 average rating, 18 reviews

Beautiful home in the heart of The Villages.

Located in the village of Buttonwood, this cozy, fully furnished home is about 5 mins away from Lake Sumter Landing,which is perfect for great food and happy hour. This home is spacious, sunny, and comes full equipped with a TV with cable, Wi-Fi, and a golf cart. The master bedroom has a private bathroom walk in closet, as well as a king -sized bed. Washer & dryer included! The house boasts tall ceilings, and a large furnished patio, perfect for lounging and grilling. Includes a BBQ grill!

Nov 6 – 13

G$25,151 GYD per night

Guest favorite

Home in Inverness

4.96 out of 5 average rating, 197 reviews

Inverness Home with a View

Relax in a clean, welcoming, home that has been updated. There are 2 fishing poles available for your use. We make sure they are in working condition and well maintained. Shopping, restaurants, and entertainment is close by. Want a beach....35 minute ride to Fort Island Trail Beach and boat ramp. We do allow hypoallergenic small dogs (2 max), non-shedding, 25 lbs. or less, each w/ proof of shot records, please bring a kennel with you. There is a non refundable $25.00 per dog fee.

Sep 3 – 10

G$21,317 GYD per night

Guest favorite

Home in Wildwood

5.0 out of 5 average rating, 14 reviews

Lovely 2BR/2BA golf cart home The Villages St Cath

Welcome to St. Catherine’s in The Villages, FL! This is a fully furnished new & contemporary 2BR/2BA house w/ golf cart to call home while you explore everything The Villages has to offer from golf to pickle-ball & clubs for any activity you can think of. Watch the gorgeous sunsets w/ a cocktail in your hand while dancing to nightly entertainment on each of the 4 town squares; you are walking distance to Sawgrass Grove. The house is equipped with everything you will need to relax & enjoy!

Oct 8 – 15

G$25,335 GYD per night

Superhost

Cottage in Wildwood

4.85 out of 5 average rating, 194 reviews

Peaceful Cottage in the Heart of Wildwood

Peaceful home... -Full kitchen for cooking any meal. A waffle iron and waffle/pancake mix provided for breakfast. -Pet friendly with $25 pet cleaning fee per pet. Notify me if bringing pet. No cats please. -Keurig coffee maker for that morning cup of joe. -WiFi and smart tv. -Washer and dryer available for use. -Large lanai with a fenced in backyard for privacy. -Extra cleaning protocols, everything is disinfected between guest. -Close to all amenities. -One mile from The Villages.

Nov 13 – 20

G$21,532 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.

Nov 28 – Dec 5

G$26,696 GYD 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

G$28,669 GYD per night

Guest favorite

Home in The Villages

4.93 out of 5 average rating, 103 reviews

Remodeled 2/2 Baja style villa w/4 person cart

4 person, yamaha gas golf cart, offered at this baja style 2 BR, 2BA courtyard villa! The villa comes fully furnished with pots, pans, linens, and it even has a blow dryer and keurig! located in the De La Vista South area just off Morse, this villa is just a short cart ride to Spanish Springs or Sumter Landing. The villa has new stainless steel appliances, beautiful plank flooring, new carpet, and paint. King bed in the master, queen bed in the guest bedroom. Both bedrooms have TV.

Aug 7 – 14

G$21,742 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!

Dec 19 – 26

G$25,408 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.

May 7 – 14

G$19,963 GYD per night

Guest favorite

Home in Wildwood

4.98 out of 5 average rating, 49 reviews

New home in the new part of the villages.

Beautiful new home in the villages. All new appliances with all brand new furniture, beds and decor. You have quick access to Sawgrass grove Entertainment facility, Ezell recreation center and McGradys pub. This open floor plan with the kitchen opening to living room keeps everyone together. The huge island is a great hanging out spot. You will have access to many close by, pools, shuffle board, parks and golf courses during your stay.

Aug 21 – 28

G$19,478 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Wildwood vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Wildwood's top sights

Lake Sumter Landing70 locals recommend

Brownwood Paddock Square53 locals recommend

The Villages Polo Club14 locals recommend

Russell Stover Chocolates4 locals recommend

Lighthouse Point Bar & Grille12 locals recommend

Olive Garden Italian Restaurant3 locals recommend

Other great vacation rentals in Wildwood

Guest favorite

Home in The Villages

5.0 out of 5 average rating, 31 reviews

Pool and fun right out back

Aug 25 – Sep 1

G$28,243 GYD per night

Guest favorite

Villa in The Villages

5.0 out of 5 average rating, 23 reviews

Palm Oasis Retreat - Pet friendly w/golf cart

Jul 31 – Aug 7

G$27,949 GYD per night

Guest favorite

Home in The Villages

4.84 out of 5 average rating, 19 reviews

Stunning Villa 2B/2B With Golf Cart

Aug 30 – Sep 6

G$22,624 GYD 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

Aug 23 – 30

G$22,409 GYD per night

Guest favorite

Home in The Villages

5.0 out of 5 average rating, 19 reviews

Haven Escape at the Village of Richmond

Jun 25 – Jul 2

G$27,204 GYD per night

Guest favorite

Home in The Villages

5.0 out of 5 average rating, 7 reviews

Courtyard Villa

Sep 21 – 28

G$17,180 GYD per night

Guest favorite

Place to stay in The Villages

5.0 out of 5 average rating, 50 reviews

Safari themed private addition with pool/hot tub.

Sep 29 – Oct 6

G$29,740 GYD per night

Guest favorite

Vacation home in Wildwood

5.0 out of 5 average rating, 16 reviews

3Bd 3Bath, Golf, Chef's Kitchen, King Bed, 2 Queen

Nov 16 – 23

G$25,852 GYD per night

Show all

Other great vacation rentals in Wildwood

Guest favorite

Home in Wildwood

4.83 out of 5 average rating, 12 reviews

Home Away from Home

Sep 7 – 14

G$31,679 GYD per night

Guest favorite

Home in The Villages

4.92 out of 5 average rating, 51 reviews

Availability starting in May! Free Golf Cart!

Jul 19 – 26

G$21,875 GYD per night

Guest favorite

Home in Lady Lake

4.94 out of 5 average rating, 35 reviews

The Villages Golf view. 3BR, 2Bath Whole house.

Jul 22 – 29

G$17,817 GYD per night

Guest favorite

Villa in The Villages

4.95 out of 5 average rating, 39 reviews

Easy Living Villa in Collier

May 25 – Jun 1

G$21,385 GYD per night

Guest favorite

Home in The Villages

5.0 out of 5 average rating, 7 reviews

New Villa in The Villages near Brownwood Square

Oct 24 – 31

G$28,838 GYD per night

Guest favorite

Home in The Villages

4.91 out of 5 average rating, 22 reviews

THE Villages, FL 3/2 Home Pet Friendly Furnished

Oct 22 – 29

G$18,790 GYD per night

Superhost

Home in Wildwood

5.0 out of 5 average rating, 6 reviews

The Villages pool property with a 4-person cart!

Sep 19 – 26

G$36,291 GYD per night

Guest favorite

Home in The Villages

4.84 out of 5 average rating, 37 reviews

Villa la Bella

Aug 16 – 23

G$15,752 GYD per night

Show all

Quick stats about vacation rentals in Wildwood

Total rentals
760 properties
Rentals with dedicated workspaces
390 properties have a dedicated workspace
Rentals with a pool
370 properties have a pool
Pet-friendly rentals
260 properties allow pets
Family-friendly rentals
670 properties are a good fit for families
Total number of reviews
11K reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Wildwood?
Yes! Work meets play with ease at over 390 vacation rentals in Wildwood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Wildwood?
Four-legged friends are welcome in Wildwood. Choose from more than 260 vacation rentals for guests traveling with pets.
Are there Wildwood vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 370 vacation homes with pools in Wildwood, available on Airbnb. Make a splash and soak up the sun in style!
Do villa rentals in Wildwood have a bbq area?
Absolutely! We offer over 40 villa rentals with a bbq area in Wildwood. Enjoy a tailored experience with all the comforts you desire.
Do villa rentals in Wildwood have a gym?
Absolutely! We offer over 30 villa rentals with a gym in Wildwood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wildwood have air conditioning?
Absolutely! We offer over 620 house rentals with air conditioning in Wildwood. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in villa rentals in Wildwood?
Experience the best of Wildwood with our villa rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Wildwood have wifi?
Absolutely! We offer over 620 house rentals with wifi in Wildwood. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Wildwood?
Wildwood has more than 550 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Villa Rentals in Wildwood?
Enhance your stay in our Villa Rentals with the most popular amenities: over 100 homes with wifi, over 100 homes with air conditioning, over 30 homes with a gym, over 40 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Wildwood vacation rentals

Top-rated vacation rentals in Wildwood

Vacation rentals for every style

Villas

Houses

Hotels

Popular amenities for Wildwood vacation rentals

Stay near Wildwood's top sights

Other great vacation rentals in Wildwood

Home in The Villages

Villa in The Villages

Home in The Villages

Villa in The Villages

Home in The Villages

Home in The Villages

Place to stay in The Villages

Vacation home in Wildwood

Other great vacation rentals in Wildwood

Home in Wildwood

Home in The Villages

Home in Lady Lake

Villa in The Villages

Home in The Villages

Home in The Villages

Home in Wildwood

Home in The Villages

Quick stats about vacation rentals in Wildwood

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Wildwood?

Are there pet-friendly vacation rentals in Wildwood?

Are there Wildwood vacation rentals on Airbnb with pools?

Do villa rentals in Wildwood have a bbq area?

Do villa rentals in Wildwood have a gym?

Do house rentals in Wildwood have air conditioning?

How much does it cost to stay in villa rentals in Wildwood?

Do house rentals in Wildwood have wifi?

Are there family-friendly house rentals in Wildwood?

What are the most popular amenities for Villa Rentals in Wildwood?

Destinations to explore