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Top Holiday Rentals in Waukeenah

Relax on a Beautiful River in a Natural Florida Setting

10.0 out of 10, Exceptional, (233)
"For an old small house on a river in Old Florida this is the real deal. Great location to parks, beaches, rivers, attractions and restaurants."
Relax on a Beautiful River in a Natural Florida Setting

Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.

10.0 out of 10, Exceptional, (11)
"Wonderful house- beautiful updates, clean, comfortable and had everything we needed! "
The price is £250
includes taxes & fees
22 Aug - 23 Aug
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.

3 Mi to Dtwn: Home w/ Yard in Tallahassee

7.4 out of 10, Good, (3)
"The house was in a nice quiet neighborhood. It had everything we needed for our stay. Kitchen had all of the staples for cooking, plenty of everything. Enjoyed the large backyard and covered deck on the back."
3 Mi to Dtwn: Home w/ Yard in Tallahassee

NEW! Last minute booking discount—close to Tallahassee Memorial Hospital

10.0 out of 10, Exceptional, (47)
"House was perfect for our needs. Clean and great service from the owners. Would absolutely stay again. "
The price is £221
includes taxes & fees
3 Sept - 4 Sept
NEW! Last minute booking discount—close to Tallahassee Memorial Hospital

New Lakeside Cabin in Tallahassee, secluded & near town

10.0 out of 10, Exceptional, (23)
"Lovely spot - recently built with quality components."
The price is £160
includes taxes & fees
14 Aug - 15 Aug
New Lakeside Cabin in Tallahassee, secluded & near town

2/2 Your Home Away From Home

9.4 out of 10, Exceptional, (13)
"Very clean property and owner was very helpful. "
2/2 Your Home Away From Home

Family Friendly! Private Full House 20 minutes to FSU

2.0 star property
10.0 out of 10, Exceptional, (7)
"The property is quiet and spacious. We have room for everyone and plenty of space to spread out. "
The price is £279
includes taxes & fees
10 Aug - 11 Aug
Family Friendly! Private Full House 20 minutes to FSU

Pet-Friendly Home Near Dtwn Tallahassee!

10.0 out of 10, Exceptional, (20)
"We had a wonderful time and we’ve stayed in many rentals, but the host here was the best of all of them. Would definitely recommend this home. "
Pet-Friendly Home Near Dtwn Tallahassee!

The Greywood | A Blackhouse Property

9.8 out of 10, Exceptional, (8)
"We have stayed at this property several times when visiting FSU. It is close enough to campus and very convenient to numerous restaurants. The house is very quaint and the neighborhood is quiet. On this last visit, Ryan was very accommodating to our schedule changes and was responsive to the chats."
The price is £169
includes taxes & fees
12 Aug - 13 Aug
The Greywood | A Blackhouse Property

Farm Buckbeak2 Tent/ScreenRoom

4.0 out of 10, (1)
"Sandy was helpful"
The price is £85
includes taxes & fees
22 Aug - 23 Aug
Farm Buckbeak2 Tent/ScreenRoom

Rare Find 3b Pet Friendly Renovated

10.0 out of 10, Exceptional, (26)
"Very Nice place but spent most of my time at THM "
The price is £252
includes taxes & fees
2 Sept - 3 Sept
Rare Find 3b Pet Friendly Renovated

Tallahassee Luxury 4 bedrooms 3.5 baths, King Bed, and Home Movie Theatre

9.8 out of 10, Exceptional, (37)
"Beautiful, clean large property! Excellent location, very nice host! Strongly recommend!"
Tallahassee Luxury 4 bedrooms 3.5 baths, King Bed, and Home Movie Theatre

Walkabout on 9 parklike acres! Special Occasions-Weddings-Reunions

2.0 star property
9.8 out of 10, Exceptional, (16)
"Fantastic place to stay!"
Walkabout on 9 parklike acres! Special Occasions-Weddings-Reunions

Tally Glamping Farmstay GIMPY’S GEODOME with mini horses, goats, cows, chickens

9.6 out of 10, Exceptional, (9)
"Great friendly camping experience. Very safe and fun experience with the animals."
Tally Glamping Farmstay GIMPY’S GEODOME with mini horses, goats, cows, chickens

Farmstay Glamping AGRItourism retreat-HERSHEYS HUT-cows, chicks, goat, minihorse

10.0 out of 10, Exceptional, (1)
"My partner and I stayed at Leroy’s Lounge and had a great time. It is such a unique experience compared to just grabbing a hotel room for a night. Had a hard time finding it in the dark after a FSU game, but Sandy was extremely helpful with directions. If you don’t mind camping, it really is an enjoyable experience. Best tent and camping experience I have ever had and appreciated the restroom and option to have a shower. Since you’re a bit outside the city, the stars were BEAUTIFUL in the...
Farmstay Glamping AGRItourism retreat-HERSHEYS HUT-cows, chicks, goat, minihorse

Beautiful Pool Home Retreat!

Beautiful Pool Home Retreat!

Clean and open 3bd/2ba in a quiet close-in neighborhood

9.8 out of 10, Exceptional, (79)
"This house was perfect for our family of 4 with two young kids. Great location and the outdoor deck is lovely. We’ll be back!"
The price is £278
includes taxes & fees
11 Aug - 12 Aug
Clean and open 3bd/2ba in a quiet close-in neighborhood

Peaceful 2 Bed, 1 Bath located in midtown, 5 miles from Stadium.

10.0 out of 10, Exceptional, (10)
"This house was very nice. It had all the things necessary to make it a great stay. "
Peaceful 2 Bed, 1 Bath located in midtown, 5 miles from Stadium.

Boho Indian Oasis: 3bd - Pool - Tranquil Retreat

7.0 out of 10, Good, (2)
"The house was 20 minutes from the fields. It worked out well. We enjoyed our stay. "
Boho Indian Oasis: 3bd - Pool - Tranquil Retreat

Camellia Cottage - wheelchair friendly

10.0 out of 10, Exceptional, (3)
"Lovely, clean, and beautifully decorated cottage within walking distance of shops and restaurants. The owners are quick to respond to messages. "
The price is £158
includes taxes & fees
11 Aug - 12 Aug
Camellia Cottage - wheelchair friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Waukeenah Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Waukeenah?

Yes, there are holiday rentals close to the most popular sights in Waukeenah, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Waukeenah has to offer?

NEW! Last minute booking discount—close to Tallahassee Memorial Hospital: This holiday home rental outside of Waukeenah offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

What can I see and do in Waukeenah?

While you're exploring the area, "Boots" Thomas Veteran Memorial Park and J. R. Alford Greenway are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find St. Marks River Preserve State Park and Monticello Opera House.

What are holiday rentals like in Waukeenah?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Waukeenah. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for family trips or small group gatherings.