10 Best Winter Haven Apartments on Holiday Lettings - Vacation rentals

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7,961 Vacation rentals

24

Villa rental in Winter Haven

Central Florida / Winter Haven

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
This home is conveniently located near Lake Eloise in Winter Haven next to the Legoland resort. This community has a boat launch with a fully stocked lake. Great for families that want to get away from the hustle and bustle of the busy resorts.This home has one queen be …see more

from $121 / night

$842 / week

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avg. 3 hours 19 minutes

from $121 / night

31

Villa rental in Winter Haven

Central Florida / Winter Haven

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly
  • Air conditioning
Stylish vacation home on Lake Eloise This vacation home is one of seven units located in Cypress Inlet, a new resort community located on Lake Eloise, in Winter Haven, FL. This vacation rental has two bedrooms, two full bathrooms and sleeps up to seven people. It featur …see more

from $138 / night

$962 / week

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Responds fast!
avg. 3 hours 19 minutes

from $138 / night

(3) Very Good 

22

Vacation villa in Winter Haven

Central Florida / Winter Haven

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Nearest beach 126 mi
  • Swimming pool
  • Child friendly
This beautiful 2615 sq.ft. 3 bedrooms, 2 bathrooms, saltwater pool home, built in 2010, sits in a gated community in the south of Winter Haven, Florida, and features everything you need for a relaxing vacation. The home provides a large fully screened heated saltwater …see more

from $142 / night

$989 - $1,395 / week

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avg. 3 hours 4 minutes

from $142 / night

(3) Excellent 

20

Vacation home in Winter Haven

Central Florida / Winter Haven

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our home has a beautiful enclosed salt water pool and is accessible by boat on the chain of lakes. 15 min to Legoland 45 min to Disney or Bush Gardens. One hour to the airports. Three Bedrooms with 2 King master suites (one with walk in shower and Jacuzzi and one with w …see more

from $258 / night

$1,804 / week

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from $258 / night

(6) Excellent 

28

Vacation home in Winter Haven

Central Florida / Winter Haven

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Nice and Cozy house next to Legoland. Enjoy this magnificent vacation home that has 3 bedrooms it will comfortably accommodate 6 guests. It has a nice back yard and the house is completely furnished and has everything you need to enjoy your vacations with us. Please …see more

from $91 / night

$571 / week

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from $91 / night

(2) Good 

12

Vacation home in Winter Haven

Central Florida / Winter Haven

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
  • Ask about pets
Welcome to the Daffodil Cottage! A brand new quaint & charming Tiny Home on beautiful Lake Mariana, located near Legoland, Disney World & Bok Tower Gardens! Come try Tiny Life enjoying included kayaks & canoe, fish, or relax around the fire pit! This is a 160 sq ft tin …see more

from $75 / night

$458 / week

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Responds fast!
avg. 2 hours 59 minutes

from $75 / night

29

Villa rental in Winter Haven

Central Florida / Winter Haven

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
This home is conveniently located near Lake Eloise in Winter Haven next to the Legoland resort. This community has a boat launch with a fully stocked lake. Great for families that want to get away from the hustle and bustle of the busy resorts.This home has one queen be …see more

from $121 / night

$842 / week

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Responds fast!
avg. 3 hours 19 minutes

from $121 / night

28

Villa rental in Winter Haven

Central Florida / Winter Haven

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning
This home is conveniently located near Lake Eloise in Winter Haven next to the Legoland resort. This community has a boat launch with a fully stocked lake. Great for families that want to get away from the hustle and bustle of the busy resorts.This home has one queen be …see more

from $121 / night

$842 / week

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Responds fast!
avg. 3 hours 19 minutes

from $121 / night

34

Villa rental in Winter Haven

Central Florida / Winter Haven

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Air conditioning
This home is conveniently located near Lake Eloise in Winter Haven next to the Legoland resort. This community has a boat launch great for families that want to get away from the hustle and bustle of the busy resorts. This home has one queen bedroom with a partitioned …see more

from $138 / night

$962 / week

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Responds fast!
avg. 3 hours 19 minutes

from $138 / night

10

Vacation home in Winter Haven

Central Florida / Winter Haven

2 5 90 nights min

  • 2 bedrooms
  • sleeps 5
  • 90 nights min
  • Air conditioning
  • Pet friendly
  • Private garden
Spacious lakefront double-wide home available for the 2017//2018 winter. 2 bedrooms, 2 baths, mud room with washer&dryer, den & Florida room, carport and large storage shed. Recently furnished and equipped. Large dining room and kitchen. Swiss Village Community, Winter …see more

from $71 / night

$495 / week

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avg. 1 hour 35 minutes

from $71 / night

33

Villa rental in Winter Haven

Central Florida / Winter Haven

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly
  • Air conditioning
This home is conveniently located near Lake Eloise in Winter Haven next to the Legoland resort. This community has a boat launch great for families that want to get away from the hustle and bustle of the busy resorts.This home has two bedrooms. A master bedroom with a k …see more

from $138 / night

$962 / week

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Responds fast!
avg. 3 hours 19 minutes

from $138 / night

Great rentals within 20 miles that match your search

Distance approx 14.21 miles from Winter Haven

(31) Very Good 

36

Vacation villa with swimming pool in Davenport

Davenport / Tivoli Manor

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our villa has 4 bedrooms (2 masters both with Queen sized beds and en suite shower rooms, and 2 further twin rooms sharing a family bathroom) so sleeps 8 comfortably. FREE HIGH SPEED INTERNET ACCESS UP TO 75Mbps WITH WI-FI (great for connecting multiple devices) and a n …see more

from $91 / night

$593 - $728 / week

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Responds fast!
avg. 3 hours 8 minutes

from $91 / night

Distance approx 16.68 miles from Winter Haven

(9) Very Good 

16

Orlando Vacation villa rental

Central Florida / Orlando

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Dream House is a beautiful 4 bedroom 3 bath two story home in the Abbey Subdivision. The Abbey is a peaceful gated community situated with only 57 other homes. The location is perfect for all central Florida attractions, with Walt Disney World only a six mile drive. …see more

from $199 / night

$1,033 - $1,106 / week

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from $199 / night

Distance approx 19.67 miles from Winter Haven

(23) Excellent 

Certificate of Excellence

92

Vacation villa with golf nearby in Davenport

Davenport / Highlands Reserve Golf Course

5 10 5 nights min

  • 5 bedrooms
  • sleeps 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Within the golfing community of Highlands Reserve just 15 minutes drive from all the fun of the Walt Disney World parks. Our comfortable family villa is fully air conditioned with 5 bedrooms and 3 bathrooms. Highlands Reserve is a beautiful and quiet community situated …see more

Certificate of Excellence

from $126 / night

$811 / week

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avg. 2 hours 34 minutes

from $126 / night

Distance approx 17.31 miles from Winter Haven

22

Davenport Vacation villa rental

Davenport / Windwood Bay

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Debbie's Orlando Villa is situated on the prestigious vacation community of Windwood Bay just a few miles from Walt Disney World and the other attractions Orlando has to offer. Surrounded by conservation land and wet lands, Lake Madison is a pleasant stroll with its nat …see more

from $140 / night

$978 / week

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from $140 / night

Distance approx 19.27 miles from Winter Haven

12

Vacation villa with indoor pool, golf nearby in Davenport

Central Florida / Davenport

4 10 5 nights min

  • 4 bedrooms
  • sleeps 10
  • 5 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
You will love our spacious 4 bedroom, 3 bathroom home located in the popular community of Sandy Ridge in Davenport. The home sleeps up to 10 guests with 2 Master bedrooms with en-suites (one King Size and One Queen), a bunk bedroom that sleeps 4, and one twin be …see more

from $148 / night

$1,033 / week

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from $148 / night

Distance approx 18.24 miles from Winter Haven

(7) Very Good 

61

Vacation condo in Davenport

Davenport / Terrace Ridge

3 7 5 nights min

  • 3 bedrooms
  • sleeps 7
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our home and excellent resort facilities are perfectly complemented by one of the most sought after locations in central Florida. Your luxury accommodation is a spacious, three bedroom, self-catering home in a gated resort, just ten minutes from Disney. This gives you …see more

from $97 / night

$629 - $916 / week

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Responds fast!
avg. 3 hours 0 minutes

from $97 / night

Distance approx 18.9 miles from Winter Haven

23

Vacation villa with golf nearby in Davenport

Davenport / Sandy Ridge

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury well maintained 4 bed 3 bath villa on the safe and secure community of Sandy Ridge. The villa has its own modern monitored alarm system and a safe.Private 30 ft x 15 ft south west facing pool with sunshine most of the day until sunset.The pool can be heated.The l …see more

from $111 / night

$774 / week

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from $111 / night

Distance approx 9.2 miles from Winter Haven Show on Map

(2) Good 

12

Vacation villa with golf nearby in Haines City

Central Florida / Haines City

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
Modern Design Villa overlooking the golf course, with 4 bedrooms and 3 bathrooms private sunny pool with spa. Unique house with 3 bedrooms in the main building and the second master bedroom is located in the "Annex Room. Complete south facing no insight from neighbors ! …see more

from $150 / night

$1,048 / week

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from $150 / night

Distance approx 16.79 miles from Winter Haven

56

Davenport Vacation home rental

Central Florida / Davenport

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Child friendly
Sitting on the stunning resort of Watersong is this modern, beautifully decorated six bedroom villa with a good-sized south facing pool deck and views of conservation and woodland to the rear of the property making this villa ideal for your family. It is exceptionally …see more

from $266 / night

$1,516 - $2,371 / week

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from $266 / night

Distance approx 12.5 miles from Winter Haven

11

Vacation apartment in Davenport

Central Florida / Davenport

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Suitable for children age 5+
The property offers a fully equipped kitchen, 2 flat screen TVs with cable and a private balcony. There is ample dining space. The master bedroom offers a King sized bed, with an ensuite bathroom. The second bedroom offers a Queen bed, also with an ensuite bathroom whil …see more

from $139 / night

$970 / week

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from $139 / night

Distance approx 9.88 miles from Winter Haven Show on Map

20

Vacation home with golf nearby in Orlando

Central Florida / Orlando

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to our Magic Villa!, This house has everything you need for a perfect vacation. It is ideally located in the 24h man-guarded community of Southern Dunes Golf and Country Club, just 20-25 minutes drive South of Disney and all other major attractions. The new bui …see more

from $207 / night

$1,031 - $2,863 / week

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Responds fast!
avg. 2 hours 29 minutes

from $207 / night

Distance approx 10.09 miles from Winter Haven Show on Map

16

Vacation home with indoor pool in Haines City

Central Florida / Haines City

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
All NEW FURNITURE Calabay park at tower lake is a beautiful community away from all central orlando traffic,and 15 minutes to Disney. Tee villa has 24/7 security for you peace of mind.includes amenities such as boat ramp,lakefront clubhouse,fishing,duck,picnic,minutes …see more

from $109 / night

$762 / week

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from $109 / night

Distance approx 17.55 miles from Winter Haven

(1) Excellent 

15

Vacation home in Davenport

Central Florida / Davenport

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Attractive, nicely decorated 4 bedroom vacation home with 3 bathrooms - ideal for family vacations! Two Master suites plus two bedrooms for the kids! TVs in all the bedrooms! Includes a private South facing swimming pool with comfortable patio furniture. Living room i …see more

from $132 / night

$922 / week

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Responds fast!
avg. 2 hours 58 minutes

from $132 / night

Distance approx 19.15 miles from Winter Haven

(1) Excellent 

17

Vacation villa in Four Corners

Central Florida / Four Corners

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Please make an enquiry before requesting a reservation as availability does frequently change, and occassionally we can offer a discounted rate. This four bedroom two bathroom pool home is located in the quiet Resort of Westridge. The villa is fully air-conditioned th …see more

from $149 / night

$951 - $1,140 / week

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Responds fast!
avg. 51 minutes

from $149 / night

Distance approx 18.53 miles from Winter Haven

42

Vacation home in Four Corners

Central Florida / Four Corners

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Property Type: House with Private Pool Floor Area: 1600 sq ft Location: FLORIDA PINES, Davenport, Disney Area Professionally managed and fully furnished vacation home property with Private Pool.. Our property has the equipment to provide your family with all the comfort …see more

from $172 / night

$1,203 / week

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Responds fast!
avg. 2 hours 54 minutes

from $172 / night

Distance approx 16.89 miles from Winter Haven

(4) Excellent 

16

Davenport Vacation villa rental

Central Florida / Davenport

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A gorgeous luxury modern new villa with 5 bedrooms, 3.5 bathrooms. This beautiful house features spacious open plan living downstairs with a fully equipped high end kitchen and light and spacious dining area. There is an air conditioned games room as well as an oversize …see more

from $172 / night

$1,203 / week

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Responds fast!
avg. 2 hours 10 minutes

from $172 / night

Distance approx 17.28 miles from Winter Haven

(5) Very Good 

21

Vacation villa with golf nearby in Davenport

Davenport / Champions Gate

9 22 min stay varies

  • 9 bedrooms
  • sleeps 22
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
This 9 bedroom 5 bathroom home will to fail to impress. It is the ultimate vacation home located in the prestigious community Champions Gate. This fabulous home accommodates up to 22 guests and close to all of the amazing attractions Florida has to offer. This outstandi …see more

from $369 / night

$2,581 / week

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Responds fast!
avg. 1 hour 23 minutes

from $369 / night

Distance approx 17.89 miles from Winter Haven

49

Davenport Vacation villa rental

Central Florida / Davenport

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Sunset Vista Villa at 133 Plumoso Loop is a beautiful, well-equipped 3 bedroom, 2 bathroom pool vacation home on wonderful Calabay Parc, close to all of Orlando's attractions. This villa has been graded "Superior" by our property management company. A huge master ensui …see more

from $126 / night

$859 / week

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from $126 / night

Distance approx 19.27 miles from Winter Haven

30

Vacation villa with golf nearby in Davenport

Central Florida / Davenport

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Private Pool - Billiard table - Game room - Cinema room projector with cable TV & Blu-ray DVD player (with Netflix and Pandora apps for your own subscriptions )- Cable TV HBO, Cinemax, Showtime, Starz, Epix, Encore, Flix. They work on TV, On Demand, and Online. Over …see more

from $194 / night

$1,355 / week

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Responds fast!
avg. 1 hour 57 minutes

from $194 / night

Distance approx 17.24 miles from Winter Haven

15

Vacation home in Davenport

Central Florida / Davenport

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Suitable for children age 5+
This very stylish single storey, 4 bedroom and 3 bathroom home is furnished to a very high standard. The home has two master bedrooms with en suite bathrooms and queen size beds and 2 guest bedrooms with two twin beds in each room. This home has a fully equipped ki …see more

from $226 / night

$1,579 / week

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from $226 / night

Distance approx 9.93 miles from Winter Haven Show on Map

23

Vacation home in Haines City

Central Florida / Haines City

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
"Play Under the Palms" is a beautiful 3 bedroom, 2 bath home with a private south facing heated and screened pool and patio that backs on the 2nd hole of the Southern Dunes Championship Golf Course. Located only 15 minutes from LEGOLAND and 20 minutes from all WALT DI …see more

from $138 / night

$859 / week

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from $138 / night

Distance approx 18.71 miles from Winter Haven

30

Home rental in Reunion with swimming pool

Central Florida / Reunion

5 13 min stay varies

  • 5 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Ask about children
This amazing spacious 5 bedroom / 5.5 Bath Vacation Holiday Home comfortable sleeps up to 10 guest. This home is fully equipped and furnished with an amazing decor along with up to date stainless steel appliances, washer and dryer, fully equipped kitchen. No …see more

from $331 / night

$2,317 / week

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Responds fast!
avg. 19 minutes

from $331 / night

Distance approx 17.24 miles from Winter Haven

(1) Excellent 

41

ChampionsGate Vacation home rental

Central Florida / ChampionsGate

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 130 mi
  • Swimming pool
  • Child friendly
Welcome to Tuscan Sunsets . . . a 5 star luxury villa with 5 bedrooms including 2 masters with en-suites. The premier location and stunning private tropical views set this home apart from the others. Enjoy morning coffee or tea as the water cascades from the spa into …see more

from $172 / night

$1,203 / week

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from $172 / night

Distance approx 18.85 miles from Winter Haven

22

Vacation home in Davenport

Central Florida / Davenport

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
This charming, air conditioned, 4 bedroom/ 3-bath home sleeps eight and has recently been refurnished and professionally decorated. The villa is conveniently located minutes from Disney, golf courses and some of the citys best shopping malls. It is also within an hours …see more

from $138 / night

$962 / week

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from $138 / night

Distance approx 19.72 miles from Winter Haven

24

Vacation villa with swimming pool in Four Corners

Central Florida / Four Corners

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Snowbirds rejoice as your quintessential Sunshine State retreat awaits you at this 5-bedroom, 3-bath Davenport vacation rental villa! Located in the desirable Highlands Reserve Golf Club, this 2-story family home is the dream Disney destination for up to 12 travelers. H …see more

from $149 / night

$1,042 / week

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Responds fast!
avg. 9 minutes

from $149 / night

Distance approx 17.24 miles from Winter Haven

15

Davenport Vacation home rental

Central Florida / Davenport

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Suitable for children age 5+
This very stylish single storey, 4 bedroom and 3 bathroom home is furnished to a very high standard. The home has two master bedrooms with en suite bathrooms and queen size beds and 2 guest bedrooms with two twin beds in each room. This home has a fully equipped ki …see more

from $226 / night

$1,579 / week

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from $226 / night

Distance approx 17.42 miles from Winter Haven

23

ChampionsGate Vacation townhouse rental

Central Florida / ChampionsGate

5 13 min stay varies

  • 5 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Car not necessary
Beautiful blues, bright and open rooms and so much more meet you here at this beautiful townhome in the resort community of Champions Gate. As you enter, you are welcomed by the openness of the home as you walk into the kitchen and dining area. The huge kitchen is outfi …see more

from $181 / night

$1,267 - $3,118 / week

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from $181 / night

Distance approx 19.47 miles from Winter Haven

22

Vacation villa with swimming pool in Four Corners

Central Florida / Four Corners

5 10 5 nights min

  • 5 bedrooms
  • sleeps 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
div class="rtejustifyAbout our Villa and Location The prestigious Highlands Reserve Golf & Leisure Community is the location of our truly luxurious executive villa. This much sought after location is ideal, be it the fun and excitement of the many theme parks or the cha …see more

from $289 / night

$2,020 / week

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from $289 / night

Distance approx 16.88 miles from Winter Haven

5

Vacation villa with swimming pool in Loughman

Central Florida / Loughman

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
p class="rtejustifyFamily Sitting Room: With sofa, 50 inch TV, Free Wireless Broadband, Internet and WiFi. Kitchen: Fully fitted kitchen with large Fridge/Freezer with ice and drinks dispenser. Fully equipped with microwave, cooker and dishwasher for all your self …see more

from $1,109 / night

$7,462 / week

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from $1,109 / night