Vacation rentals in Howey-in-the-Hills

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Top-rated vacation rentals in Howey-in-the-Hills

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Guest favorite

Guesthouse in Leesburg

4.98 out of 5 average rating, 333 reviews

Silver Lake Guest Pool House

The Silver Lake Pool Guest house Is your home away from home 1400 sq feet plenty of room! The pool house is a peaceful place to relax or take a swim in a large salt water pool . Mt Dora Tavares, Eustis 10 to 15 minutes away from Pool house Forty five minutes Daytona, Tampa Smyrna beach and parks Minutes from grocery stores restaurants malls Full kitchen also grilling. We are happy to help you with your needs ! Home is great for couples families, solo adventurers, and business travelers.

Oct 16 – 23

G$20,921 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.

May 22 – 29

G$21,214 GYD per night

Guest favorite

Farm stay in Howey-in-the-Hills

4.96 out of 5 average rating, 96 reviews

Private Getaway on the Hilltop

Our small apartment is on a 20 acre tree farm at the top of one of the highest hills in florida. We are perfectly situated in the middle of bicyclist heaven with many challenging hills just outside our gated property. Enjoy all Central Florida has to offer within a short drive... Mt. Dora, with its cute shops, Clermont, Choice of Champions training, Disney is less than 45 minutes away and either coast just over 1 hour. Private, just remodeled, and cozy ground floor entrance w/ 2nd floor living.

Oct 15 – 22

G$18,448 GYD per night

Guest favorite

Guesthouse in Clermont

4.98 out of 5 average rating, 101 reviews

Downtown Apartment - Walk to Lake, Shops & Dining

This stylish apartment, in Downtown Clermont is @ the center of the coast-to-coast bike trail. Enjoy the quaint lake town experience to the fullest without having to drive anywhere. Lakefront, breweries, retail, dining- all within a 3 min walk! Best features indoors include comfy beds, a double shower, smart TV, & cozy aesthetics. The space is well stocked w/ all the essentials. Small appliances for cooking include an air fryer, crockpot & skillet. Garage storage available 4 recreational gear.

May 11 – 18

G$28,170 GYD per night

Guest favorite

Guesthouse in Tavares

4.98 out of 5 average rating, 63 reviews

The Landing Pad+Low Cleaning Fee

LOW CLEANING FEES!!! We are located in heart of Taveras where everything is walking distance-restaurants, pubs, the seaport, Wooton Park & the history museum! Sit on the patio while using the electric grill. Bring your boat! Plenty of off street park with easy access using the alleyway. Bathroom has a rain shower with 2 speeds. Full kitchen including all the basic amenities+kureig with refillable cups. Come & relax at this fun little spot & enjoy all we have to offer thanks for landing here!

Sep 26 – Oct 3

G$18,258 GYD per night

Guest favorite

Townhouse in Clermont

4.93 out of 5 average rating, 191 reviews

Paradise Escape

Your paradise escape is finally here! In the Sunshine State, paradise is just one perfect cocktail away. Leave your worries away and relax - you are in a sunshine state of mind! My "paradise island" is conveniently located in the heart of Clermont. You will certainly enjoy the welcoming and colorful ambiance! Combination lock instructions will be sent after arrival time confirmation. I look forward to hosting all my guests and making sure that they have an unforgettable experience!

Jun 2 – 9

G$22,242 GYD per night

Guest favorite

Home in Howey-in-the-Hills

4.88 out of 5 average rating, 26 reviews

Howey in the hills Home next to Howey Mansion

Looking for a 5-star stay with a less than 1 mile walk to the Howey Mansion and Mission inn? Our centrally located 3 bedroom Howey In The Hills House with a large fully fenced yard will be just that. Immaculately clean with fresh linens this home away from home will be everything you wanted and more. Bring the whole family to our lovely home with lots of room for fun. Located close to The Harris chain of lakes, Tavares, Mount Dora, The Villages, Disney, and the list goes on!

Aug 1 – 8

G$25,814 GYD per night

Guest favorite

Guesthouse in Mount Dora

4.9 out of 5 average rating, 704 reviews

Key West cottage of Mt Dora

Cozy little cottage located in the gardens of the main house. It has a full kitchen. 1 bath with a jacuzzi tub.. Queen size bed and a couch for a 3rd person. THE LOCATION is 3 MILES between Mount Dora ,Tavares & Eustis a short drive or bike ride to all location. I’m 2.5 blocks off Lake Shore Dr. to beautiful Lake Dora. FRESH eggs from the Easter egg hens for your use ( When available) The eggs they lay are pink, green and blue. They will need to be washed before use..

Jan 27 – Feb 3

G$28,362 GYD per night

Guest favorite

Cottage in Tavares

4.92 out of 5 average rating, 131 reviews

Cypress Boathouse Retreat

A retreat atop a real boathouse overlooking a beautiful canal which leads to the Dead River. The Dead River connects Lake Harris and Lake Eustis. The Harris Chain of Lakes attracts the pro bass fisherman. Many pro fishing tournaments are held in these amazing lakes. While at the boathouse you might experience beautiful nature such as osprey, eagles, owls, and many other species of animals. Location is a short ride to the world famous Leesburg Bike Fest.

Jan 16 – 23

G$25,530 GYD per night

Guest favorite

Guesthouse in Tavares

4.96 out of 5 average rating, 72 reviews

Peaceful, adorable, guest cottage on Apopka Canal.

This special place with an "out in the country" feel is actually close to everything, making it easy to plan your visit. It is close to the cute shops and restaurants of Mt. Dora and Tavares, yet only an hour from all the attractions in the Orlando area. This 15 acre peace of paradise is right on the Apopka Canal with easy access to the Harris Chain of Lakes. Launch your boat from the boat ramp just across the canal from The Acorn at Lake Jem park.

Jan 31 – Feb 7

G$18,071 GYD per night

Guest favorite

Cottage in Tavares

4.97 out of 5 average rating, 204 reviews

Lakeside Cottage on Lake Dora

A charming 1200 sq ft, two bedroom, two bath cottage located on beautiful Lake Dora with white sand beach. A great place to relax and your home away from home. Just minutes from Tavares (known as the Seaplane City) and Mt. Dora (known as the City of Festivals.) You can bring your boat and tie it up to the dock. Large circular drive with plenty of parking for cars, trailers, etc.

Nov 22 – 29

G$29,491 GYD per night

Guest favorite

Home in Eustis

4.97 out of 5 average rating, 108 reviews

Waterfront with Boat Dock! Fishing and Summer Fun!

The Acorn is a charming 2/2 canal front bungalow with direct access to Lake Eustis. Secure parking for trucks and trailers. Ready for bass tournaments or a weekend at the Dora sandbar. Visit the lakeside restaurants on the beautiful Harris Chain of Lakes when you're ready for a cold drink or a meal. Just 45 minutes to Orlando if you feel the need to go to town.

May 6 – 13

G$31,663 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Howey-in-the-Hills vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Howey-in-the-Hills's top sights

Mission Inn Resort & Club12 locals recommend

The Howey Mansion4 locals recommend

JB Boondock's Bar & Grill8 locals recommend

Other great vacation rentals in Howey-in-the-Hills

Guest favorite

Apartment in Minneola

4.97 out of 5 average rating, 30 reviews

Private Cedar Hideaway in the Hills

Jan 14 – 21

G$22,979 GYD per night

Guest favorite

Guesthouse in Deer Island

4.93 out of 5 average rating, 82 reviews

Sapphire Cottage - sleeps 4, on 5 acres with canal

May 10 – 17

G$26,391 GYD per night

Guest favorite

Home in Tavares

5.0 out of 5 average rating, 18 reviews

Lake Harris Getaway

Jul 29 – Aug 5

G$30,871 GYD per night

Guest favorite

Apartment in Minneola

4.98 out of 5 average rating, 48 reviews

Spacious Apartment In Minneola

Aug 20 – 27

G$18,927 GYD per night

Guest favorite

Home in Leesburg

5.0 out of 5 average rating, 32 reviews

Waterfront cottage Haynes Creek

Jul 9 – 16

G$22,699 GYD per night

Guest favorite

Apartment in Clermont

4.92 out of 5 average rating, 52 reviews

Relaxing 1-Bedroom Farm Retreat. Pets welcome!

Feb 2 – 9

G$19,080 GYD per night

Guest favorite

Home in Clermont

5.0 out of 5 average rating, 9 reviews

Unique 1 BR home/55+ Community

Oct 5 – 12

G$19,485 GYD per night

Guest favorite

Guesthouse in Groveland

4.93 out of 5 average rating, 69 reviews

The Blue Apartment - Country living & lake access.

Nov 19 – 26

G$22,820 GYD per night

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Quick stats about vacation rentals in Howey-in-the-Hills

Total rentals
10 properties
Local attractions
Mission Inn Resort & Club, The Howey Mansion, and JB Boondock's Bar & Grill
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Total number of reviews
260 reviews
Nightly prices starting at
G$20,856 GYD before taxes and fees

Vacation rentals in Howey-in-the-Hills

Top-rated vacation rentals in Howey-in-the-Hills

Guesthouse in Leesburg

Home in Lady Lake

Farm stay in Howey-in-the-Hills

Guesthouse in Clermont

Guesthouse in Tavares

Townhouse in Clermont

Home in Howey-in-the-Hills

Guesthouse in Mount Dora

Cottage in Tavares

Guesthouse in Tavares

Cottage in Tavares

Home in Eustis

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Howey-in-the-Hills vacation rentals

Stay near Howey-in-the-Hills's top sights

Other great vacation rentals in Howey-in-the-Hills

Apartment in Minneola

Guesthouse in Deer Island

Home in Tavares

Apartment in Minneola

Home in Leesburg

Apartment in Clermont

Home in Clermont

Guesthouse in Groveland

Quick stats about vacation rentals in Howey-in-the-Hills

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore