Wildwood vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Wildwood

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

Guest favorite

Tiny home in Inverness

4.97 out of 5 average rating, 233 reviews

The Love Shack at The Cove

The "Love Shack," (at The Cove) is our latest project. Approximately 400 sq. feet and originally built as a cabin for the fish camp. Completely remodeled the cabin is decorated with vintage furniture, granite countertops, live edge oak shelving, a smart TV and large shower. Nestled under hugh live oaks and surrounded by decking is perfect for that morning coffee or evening glass of wine. Dog friendly with 25lb or less weight. NO CATS! $25 fee

Sep 20 – 27

R2,311 ZAR per night
Guest favorite

Villa in The Villages

4.87 out of 5 average rating, 70 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.

Jun 13 – 20

R2,110 ZAR per night
Guest favorite

Home in Lady Lake

4.97 out of 5 average rating, 266 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.

Jul 27 – Aug 3

R1,720 ZAR per night

Popular amenities for Wildwood vacation rentals

Stay near Wildwood's top sights

Lake Sumter Landing70 locals recommend
Brownwood Paddock Square53 locals recommend
Russell Stover Chocolates4 locals recommend
Lighthouse Point Bar & Grille12 locals recommend
Olive Garden Italian Restaurant3 locals recommend
Cody's Original Roadhouse - Brownwood8 locals recommend

Other great vacation rentals in Wildwood

Guest favorite

Home in Inverness

4.9 out of 5 average rating, 72 reviews

Inverness 2 bedroom/2 bathroom featuring a hot tub

Dec 7 – 14

R2,115 ZAR per night
Superhost

Villa in The Villages

4.89 out of 5 average rating, 9 reviews

New 3/2 Patio Villa, BEST VALUE w/Golf Cart!

Jun 8 – 15

R2,215 ZAR per night
Guest favorite

Cabin in Center Hill

4.96 out of 5 average rating, 28 reviews

Woodsy cabin close to major theme parks

Aug 5 – 12

R2,297 ZAR per night
Guest favorite

Home in The Villages

4.88 out of 5 average rating, 16 reviews

Stunning Villa 2B/2B With Golf Cart

Sep 4 – 11

R2,055 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

Jul 22 – 29

R2,109 ZAR per night
Guest favorite

Home in The Villages

5.0 out of 5 average rating, 31 reviews

Pool and fun right out back

Sep 9 – 16

R2,713 ZAR per night
Guest favorite

Villa in The Villages

4.93 out of 5 average rating, 57 reviews

The Haven

Jun 24 – Jul 1

R1,783 ZAR per night
Guest favorite

Villa in The Villages

4.97 out of 5 average rating, 30 reviews

3/2 Courtyard Villa w/Golf Cart Walk to Brownwood!

Jun 29 – Jul 6

R2,097 ZAR per night
Superhost

Home in The Villages

4.85 out of 5 average rating, 68 reviews

Inspire Retire - The Newest Side of the VillageS

Aug 5 – 12

R1,988 ZAR per night
Guest favorite

Place to stay in The Villages

5.0 out of 5 average rating, 48 reviews

Safari themed private addition with pool/hot tub.

Apr 20 – 27

R3,072 ZAR 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

Aug 21 – 28

R2,387 ZAR per night
Guest favorite

Home in The Villages

4.84 out of 5 average rating, 37 reviews

Villa la Bella

Jul 15 – 22

R1,625 ZAR per night

Other great vacation rentals in Wildwood

Guest favorite

Villa in The Villages

4.98 out of 5 average rating, 54 reviews

Perfect location Lake Sumpter Villa w/ Golf Cart

Nov 8 – 15

R2,521 ZAR per night
Guest favorite

Home in The Villages

4.92 out of 5 average rating, 12 reviews

Cheerful King Bed Home in the Villages

Oct 12 – 19

R2,193 ZAR per night
Superhost

Villa in The Villages

4.78 out of 5 average rating, 9 reviews

Cheerful 2 Bedroom Villa with a GREAT Location!

May 16 – 23

R1,958 ZAR per night
Guest favorite

Vacation home in Wildwood

5.0 out of 5 average rating, 14 reviews

New, Trending, Golfing, Chef's kitchens, Designer

Sep 19 – 26

R2,343 ZAR per night
Guest favorite

Home in Lady Lake

4.94 out of 5 average rating, 36 reviews

One Bedroom Courtyard Villa in The Villages

Jan 28 – Feb 4

R3,241 ZAR per night
Guest favorite

Home in The Villages

5.0 out of 5 average rating, 28 reviews

The Pelican House

Nov 2 – 9

R2,444 ZAR per night
Guest favorite

Home in Inverness

4.95 out of 5 average rating, 42 reviews

Jack & Jill’s clean & cute home on private lot.

Aug 4 – 11

R2,058 ZAR per night
Guest favorite

Home in The Villages

5.0 out of 5 average rating, 16 reviews

Beautiful Designer Home -Golf Cart- Walk to Sumter

Jun 20 – 27

R2,465 ZAR per night
Guest favorite

Home in The Villages

5.0 out of 5 average rating, 15 reviews

The Villages (walk to pool, Lake Sumter SQ 2 MI)

Jul 18 – 25

R2,867 ZAR 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

Sep 6 – 13

R1,707 ZAR per night
Guest favorite

Home in The Villages

4.94 out of 5 average rating, 35 reviews

Beautiful Villages 2/2 Home. Perfect Location

Jul 3 – 10

R1,873 ZAR per night
Guest favorite

Home in Lady Lake

4.94 out of 5 average rating, 17 reviews

Relaxing House in The Villages

Sep 29 – Oct 6

R1,246 ZAR per night

Quick stats about vacation rentals in Wildwood

Total rentals

760 properties

Rentals with dedicated workspaces

400 properties have a dedicated workspace

Rentals with a pool

360 properties have a pool

Pet-friendly rentals

260 properties allow pets

Family-friendly rentals

660 properties are a good fit for families

Total number of reviews

10K reviews

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Wildwood?

    Yes! Work meets play with ease at over 400 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 360 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 house rentals in Wildwood have a gym?

    Absolutely! We offer over 120 house rentals with a gym in Wildwood. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Wildwood have air conditioning?

    Absolutely! We offer over 110 villa 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 610 house rentals with wifi in Wildwood. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly villa rentals in Wildwood?

    Wildwood has more than 100 family-friendly villa 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 20 homes with a gym, over 110 homes with wifi, over 40 homes with a bbq area, over 110 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sumter County
  5. Wildwood