Howey in the Hills Rentals

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172 Houses

(1) Excellent 

24

NEW! Gated Guesthouse at Historic Howey Mansion!

Lake County / Howey in the Hills

Howey in the Hills house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$229

Responds fast!
avg. 7 minutes

Price per night from

$229

18

5 Acre Private Gated Estate with pool, game room and theater room near Disney

Lake County / Howey in the Hills

Howey in the Hills house

10 24 5 nights min

  • 10 bedrooms
  • sleeps 24
  • 5 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$999

Price per night from

$999

Great rentals within 20 miles that match your search

Distance approx 3.02 km from Howey in the Hills Show on Map

(3) Very Good 

50

3/2 1920s Lake Estate w/Access to Pool, Gym & Boat

Lake County / Yalaha

Yalaha house

3 9 3 nights min

  • 3 bedrooms
  • sleeps 9
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$190

Price per night from

$190

Distance approx 15.43 km from Howey in the Hills

24

NEW! Clermont Condo by Lake Louisa- Mins to Disney

Lake County / Clermont

Clermont condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$92

Responds fast!
avg. 8 minutes

Price per night from

$92

Distance approx 9.79 km from Howey in the Hills

18

1880's Vintage Home next to Downtown and Lakefront.

Lake County / Mount Dora

Mount Dora villa

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Air conditioning
  • Pet Friendly
  • Private garden

Price per night from

$173

Responds fast!
avg. 2 hours 4 minutes

Price per night from

$173

Distance approx 17.05 km from Howey in the Hills

(5) Excellent 

32

The Villages Village of Duval Relax and Play in the Middle Of Paradise

Florida / The Villages

The Villages house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Car not necessary
  • Air conditioning
  • Private garden
“Lucky me to have happened upon one of the nicest rentals in The Villages.” This rental was perfect for me in every way. A great location in Duval, easy quick access to the pool, quiet neighborhood. The villa was immaculate ** with a lovely decor, gene
…see more

Price per night from

$114

Price per night from

$114

Distance approx 10.64 km from Howey in the Hills

26

Waterfront Front Rental With Pontoon Boat, Dock an

Lake County / Leesburg

Leesburg house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$151

Price per night from

$151

Distance approx 7.69 km from Howey in the Hills

9

Fully Furnished House Orlando Florida

Central Florida / Orlando

Orlando house

2 6 30 nights min

  • 2 bedrooms
  • sleeps 6
  • 30 nights min
  • Nearest beach 130 mi
  • Swimming pool
  • Child Friendly

Price per night from

$64

Price per night from

$64

Distance approx 7.03 km from Howey in the Hills

(9) Excellent 

18

Fox Haven Cottage

Lake County / Tavares

Tavares cottage

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Ask about children
  • Air conditioning

Price per night from

$66

Responds fast!
avg. 2 hours 47 minutes

Price per night from

$66

Distance approx 3.78 km from Howey in the Hills Show on Map

13

Standing 30 Ft Travel Trailer

Lake County / Clermont

Clermont caravan/mobile home

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$81

Price per night from

$81

Distance approx 16.55 km from Howey in the Hills

24

Designer Home at The Villages - Near Brownwood

Florida / Wildwood

Wildwood house

3 4 28 nights min

  • 3 bedrooms
  • sleeps 4
  • 28 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$91

Responds fast!
avg. 8 minutes

Price per night from

$91

Distance approx 19.59 km from Howey in the Hills

22

Country Living at Webster Country Cottages - The Birdhouse

Florida / Webster

Webster house

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$231

Responds fast!
avg. 54 minutes

Price per night from

$231

Distance approx 4.29 km from Howey in the Hills Show on Map

(55) Excellent 

25

The Sweet Escape - 10 Bedrooms on 5 Acres!

Lake County / Clermont

Clermont villa

10 50 3 nights min

  • 10 bedrooms
  • sleeps 50
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Awesome experience!” This house is unbelievable! the decoration of it has so many details that i still discovered some of them after been there for 2 weeks... The decoration, the spacing, the activities... everything is perfect for a large group (we w
…see more

Price per night from

$1,201

Responds fast!
avg. 2 hours 50 minutes

Price per night from

$1,201

Distance approx 18.5 km from Howey in the Hills

8

Spanish Springs Courtyard Villa

Florida / The Villages

The Villages villa

2 3 7 nights min

  • 2 bedrooms
  • sleeps 3
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$99

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$99

Distance approx 6.9 km from Howey in the Hills

17

The Cardinals Rest at Lake Dora Close to Everything There is to Do in Florida

Lake County / Mount Dora

Mount Dora house

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 102 mi
  • Swimming pool

Price per night from

$302

Responds fast!
avg. 1 hour 59 minutes

Price per night from

$302

Distance approx 18.24 km from Howey in the Hills

16

Hilltop House on 400-acre Resort

Lake County / Lady Lake

Lady Lake house

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$259

Price per night from

$259

Distance approx 16.16 km from Howey in the Hills

(16) Excellent 

42

EXCLUSIVE LUXURY RESORT HOME MINUTES FROM DISNEY

Central Florida / Kissimmee

Kissimmee house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great Stay” Enjoyed the accommodations offered by your property. Was exactly what I expected, except for a few deficiencies, such as carpet needed cleaning on stairs and in some areas, DVD player wouldn’t work in my bedroom. I cleaned up, stripped bed
…see more

Price per night from

$184

Responds fast!
avg. 2 hours 54 minutes

Price per night from

$184

Distance approx 15.57 km from Howey in the Hills

24

The Village of Sanibel Cottage w/ Enclosed Lanai!

Florida / The Villages

The Villages cottage

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$110

Responds fast!
avg. 8 minutes

Price per night from

$110

Distance approx 18.49 km from Howey in the Hills

6

Newly Remodeled Historic Village Prop

Lake County / Lady Lake

Lady Lake house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Air conditioning
  • Pet Friendly

Price per night from

$202

Price per night from

$202

Distance approx 18.28 km from Howey in the Hills

23

Beautiful 3 Br Designer Home In Sunset Pointe

Florida / The Villages

The Villages house

3 2 30 nights min

  • 3 bedrooms
  • sleeps 2
  • 30 nights min
  • Nearest beach 112 mi
  • Swimming pool
  • Ask about children

Price per night from

$165

Responds fast!
avg. 2 hours 45 minutes

Price per night from

$165

Distance approx 13.05 km from Howey in the Hills

13

The Retreat at Swiss

Lake County / Clermont

Clermont house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 128 mi
  • Swimming pool
  • Child Friendly

Price per night from

$173

Responds fast!
avg. 2 hours 58 minutes

Price per night from

$173

Distance approx 7.08 km from Howey in the Hills

26

NEW! Chic Tavares Home w/Private Dock on Lake Dora

Lake County / Tavares

Tavares house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$156

Responds fast!
avg. 8 minutes

Price per night from

$156

Distance approx 19.34 km from Howey in the Hills

11

Welcome to Tee Off Villa - Beautiful 2 Bdrm/2 Bath on Golf Course w/Cart & Spa

Florida / The Villages

The Villages house

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$87

Price per night from

$87

Distance approx 19.68 km from Howey in the Hills

29

Serene Country Club Home w/Golf Cart in Lady Lakes

Lake County / Lady Lake

Lady Lake house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$101

Responds fast!
avg. 10 minutes

Price per night from

$101

Distance approx 16.59 km from Howey in the Hills

23

3002 Gallinule Court

Florida / Coleman

Coleman villa

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$125

Responds fast!
avg. 3 hours 45 minutes

Price per night from

$125

Distance approx 17.82 km from Howey in the Hills

45

Lakefront Dream Vacation Rental With Your Own Private Sandy Beach

Lake County / Umatilla

Umatilla house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$403

Responds fast!
avg. 21 minutes

Price per night from

$403

Distance approx 15.41 km from Howey in the Hills

40

NEW for 2018 3-UP SPARK and separate deck overlooking Lake NO EXTRA CLEANING FEE

Lake County / Clermont

Clermont cottage

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Nearest beach 0.05 mi
  • Child Friendly
  • Air conditioning

Price per night from

$207

Price per night from

$207

Distance approx 17.01 km from Howey in the Hills

7

Perfectly Situated on Poppy

Florida / The Villages

The Villages house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$108

Responds fast!
avg. 3 hours 45 minutes

Price per night from

$108

Distance approx 11.4 km from Howey in the Hills Show on Map

11

This Orange Tree 5/4 pool home is the epitome of comfort! Great deck, spa and

Lake County / Clermont

Clermont house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Suitable for children age 5+

Price per night from

$213

Price per night from

$213

Distance approx 11.4 km from Howey in the Hills Show on Map

15

High Grove 4/3 pool home property, fully furnished, with full kitchen, and all

Lake County / Clermont

Clermont house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Suitable for children age 5+

Price per night from

$197

Price per night from

$197

Distance approx 18.31 km from Howey in the Hills

13

Beautiful 2/2 - Best Location in The Villages

Florida / The Villages

The Villages house

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Air conditioning
  • Pet Friendly
  • Private garden

Price per night from

$46

Price per night from

$46

Distance approx 19.54 km from Howey in the Hills

(2) Excellent 

12

DESIRABLE LOCATION WINIFRED VILLAGE DESIGNER HOME

Florida / The Villages

The Villages house

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$58

Price per night from

$58

Distance approx 13.74 km from Howey in the Hills

28

8 Bedrooms with Games Table 1943NC

Lake County / Clermont

Clermont villa

8 16 5 nights min

  • 8 bedrooms
  • sleeps 16
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$346

Responds fast!
avg. 2 hours 55 minutes

Price per night from

$346

Distance approx 15.41 km from Howey in the Hills

55

The cottage on Lancaster Beach 8 miles from Disney's Western Entrance

Lake County / Clermont

Clermont house

5 14 1 night min

  • 5 bedrooms
  • sleeps 14
  • 1 night min
  • Nearest beach 0.05 mi
  • Child Friendly
  • Air conditioning

Price per night from

$251

Price per night from

$251

Distance approx 11.4 km from Howey in the Hills Show on Map

13

The fun doesn't have to stop when you leave the theme parks! This Orange Tree

Lake County / Clermont

Clermont house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Suitable for children age 5+

Price per night from

$213

Price per night from

$213

Distance approx 11.4 km from Howey in the Hills Show on Map

11

Greater Groves 4/2 pool home with ample space for the whole family. Near

Lake County / Clermont

Clermont house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Suitable for children age 5+

Price per night from

$172

Price per night from

$172

Distance approx 16.23 km from Howey in the Hills

(1) Excellent 

10

A lovely & cozy home centrally located

Florida / The Villages

The Villages house

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$92

Price per night from

$92

Distance approx 17.33 km from Howey in the Hills

19

The Villages, Liberty Park, 2 Bedrooms/Den

Florida / The Villages

The Villages house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$115

Price per night from

$115