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Guesthouse vacation rentals in DeLand

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Top-rated guesthouse rentals in DeLand

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

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Top guest favorite
A private tropical pool area is framed by lush greenery and vibrant plants, complemented by a stone water feature. The sparkling water reflects sunlight, creating a serene atmosphere. Loungers are positioned nearby for relaxation, inviting guests to enjoy the tranquil setting.
Guesthouse in Port Orange
4.94 out of 5 average rating, 368 reviews

Relaxing Tropical Pool Get Away Suite

Relaxing Tropical themed pool, spa with grilling area and tiki bar. Private secure parking space near detached suite with gated entry code access. Centrally located to all main area attractions and events. Coffee, shopping, and walking distance from the popular local restaurants and drinking establishments, also two waterfront dog walking parks in the neighborhood. Only 2 miles to beachside. Our home away from home resort is the perfect place to find peace, tranquility and a short stay getaway.

Top guest favorite
The inviting exterior features a two-story home framed by lush green grass and mature trees. Arched windows and a symmetrical design enhance the charm, while a driveway leads to the front entrance, providing easy access to the peaceful surroundings.
Guesthouse in Leesburg
4.98 out of 5 average rating, 407 reviews

Silver Lake Guest Pool House Very Private !

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

Guest favorite
Guesthouse in Sanford
4.95 out of 5 average rating, 168 reviews

Little Hidden Cottage- Near Sanford Airport

Located in Sanford FL, our Hidden Little Cottage is a private studio guest house with its own entrance, features full kitchen & bath room, queen size bed, full size pull out couch & twin size travel bed, & provides flexible self check-in. We are located 7 minutes from the Sanford Airport and Boombah Sports Complex, 10 minutes to Downtown Sanford, I –4 & 4–17. We’re also central to many Central Florida attractions such as Natural Springs, Sandy Beaches, Theme Parks and Historic Districts

Guest favorite
A serene view of Lake Mary is framed by a large tree and a white post. The sky transitions into vibrant hues as the sun sets, reflecting softly on the water's surface. A lamp illuminates the foreground, enhancing the peaceful lakeside atmosphere.
Guesthouse in Lake Mary
4.97 out of 5 average rating, 123 reviews

Sunset Cottage in Lake Mary, Florida

Located on beautiful Lake Mary, this completely renovated studio sized guest house offers beautiful sunsets over the lake from a private patio. A comfortable queen bed, stylish sitting area and fully stocked kitchenette make for a wonderful stay in the Lake Mary- Sanford area. Minutes from the Sanford airport, close to the Sunrail station and 45 minutes to either Disney World or the beach. Our guest cottage is a perfect place to visit. Please note: The cottage is lakeview only.

Guest favorite
The spacious room features a queen bed dressed in crisp white linens, flanked by two blue accent chairs. A large area rug adds comfort underfoot. Natural light streams in through a nearby window, and a ceiling fan provides a cooling breeze. A small dining area is also visible.
Guesthouse in Sanford
4.93 out of 5 average rating, 119 reviews

Suite Retreat

Avoid blah hotels with high prices and stay in this luxe new apartment suite! It’s a perfect retreat in Central Florida. Located a short drive to activities, restaurants, & shops in Lake Mary or downtown Sanford - 45-55 min to Orlando theme parks or the beaches of New Smyrna. Ideal for a couple’s retreat or a getaway for one. Guests use office space designed for comfort & productivity. A cozy chair begs readers to curl up and read. The outdoor canopy hosts breakfast with birdsong!

Superhost
A wooden deck area features a mural depicting a serene waterside scene. Two large glass doors provide access to the interior, while tropical plants add a touch of greenery. A long, dark fire pit table sits centrally, ready for gatherings.
Guesthouse in Orange City
4.85 out of 5 average rating, 162 reviews

Tropical Cottage & Garage 2 Miles from Blue Spring

This cozy spring escape sits privately behind a unoccupied garage among the quiet oak streets of Orange city. conveniently located 2 miles from Blue springs state park, 5 miles from Downtown Deland and 30 minutes from the beautiful beaches of Daytona and New Syrmrna. This property provides a unique connection to nature. Enjoy an outdoor bathroom experience with a shower under the stars. Blue Springs is now open for swimming & water fun as of May 23, 2025! Garage amenities included!

Top guest favorite
A serene pool area features a vibrant red pool float resting in the clear water, surrounded by lush greenery. Comfortable outdoor seating is arranged near the pool, with large umbrellas providing shade. The backdrop showcases a charming pool house with multiple glass doors, inviting natural light.
Guesthouse in Lake Eola Heights
5 out of 5 average rating, 261 reviews

Livingston Pool House- In The Heart of Downtown

Welcome to the Pool House! Our newly renovated detached pool house is located in the heart of downtown Orlando, in the Lake Eola Heights Historic District. We are two blocks to beautiful Lake Eola and all the dining and entertainment that Orlando has to offer. The Pool House has everything you need for a relaxing time at home, yet all the entertainment at your finger tips! Downtown living with a tropical escape!

Top guest favorite
The entrance of the cottage is highlighted by a warm glow from the inviting red door. Decorative curtains frame the entrance, complemented by a pathway lined with greenery and potted plants, creating a welcoming ambiance as evening falls.
Guesthouse in Lake Helen
4.95 out of 5 average rating, 247 reviews

Hidden Gem - Cottage in Lake Helen

Nestled in a beautiful paved and gardened backyard space. My 640 sq/ft private cottage is behind my home in the small quiet town of Lake Helen, only a mile off of I-4. The cottage is filled with all the amenities that will make you feel at home. The cottage has one queen bed and the sofa bed is perfect for children. Also a pack and play for little ones. The cottage is perfect for two but will suit 4.

Top guest favorite
A mid-century modern home is illuminated at dusk, showcasing its distinctive architectural features. Large glass windows reflect the evening light, while the warm glow from interior lighting enhances the inviting exterior. Lush landscaping surrounds the house, providing a serene atmosphere.
Guesthouse in Maitland
4.97 out of 5 average rating, 171 reviews

Private 1-bd Mid-Century Guesthouse

Welcome to our tranquil & private 1-bd Mid-Century Modern Guesthouse. The space has a separate entrance and keyless access. Full kitchen, living room, bedroom and bathroom. Centrally located in Florida, our guesthouse offers easy access to the surrounding areas. Lots of museums, nature walks, parks & fantastic places to eat. Book now & experience the love & care we have put into our property!

Guest favorite
A quaint cottage exterior is surrounded by landscaped grounds featuring a seating area with a small white table and two chairs. Potted plants and decorative mulch create a welcoming space, with a solid red wood finish on the building and a single door framed by two windows.
Guesthouse in De Leon Springs
4.93 out of 5 average rating, 147 reviews

Cottage on horse farm

Casual cottage on horse farm in rural setting. Stroll through the flower gardens and paddock lanes of the 30 acre horse farm. Watch horses trained dressage. Country atmosphere but still only 10 minutes to grocery store, 5 minutes to restaurants, 15 minutes to historical downtown Deland, Stetson University & skydive Deland. 30 minutes to Daytona Speedway, 45 minutes to the beach. NO WI-FI

Top guest favorite
A cozy studio features a spacious bed with a decorative blue and white coverlet. Natural light streams through the floral-patterned curtains, illuminating the wood-grain flooring. A ceiling fan, air conditioning unit, and various furniture pieces provide comfort and functionality within the inviting space.
Guesthouse in DeLand
4.9 out of 5 average rating, 494 reviews

The Cottage at True Trail Farm

Our studio Cottage is pet friendly and sleeps 2 comfortably. This is a tiny house where we have managed to fit all essentials for a relaxing stay. We are 5 minutes from historic downtown and 30 minutes to the World’s Most Famous Beach, Daytona Beach. Enjoy fresh eggs from our chickens in the morning before heading to the Springs for a cool dip or manatee watching only 10 minutes away.

Guest favorite
The room features a spacious bed with a neutral-colored quilt, flanked by two wooden nightstands that hold lamps. Natural light enters through a large window with blinds, casting a soft glow on the tiled floor.
Guesthouse in De Leon Springs
4.8 out of 5 average rating, 179 reviews

Serene DeLeon Springs Studio Getaway

Stay in a private studio apartment in DeLeon Springs, FL, perfect for solo travelers or couples. This cozy space includes a full kitchen, private bathroom, TV, and internet, offering everything you need for a comfortable stay. Just minutes from DeLeon Springs State Park, Daytona International Speedway, and Daytona Beach, with Orlando’s theme parks about an hour away.

Popular amenities for DeLand guesthouse rentals

Quick stats about guesthouse rentals in DeLand

  • Total rentals

    10 properties

  • Nightly prices starting at

    € 43 before taxes and fees

  • Total number of reviews

    1.9K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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