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

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, 402 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

Top guest favorite

A serene pool area is surrounded by lush tropical greenery, including palm trees and bamboo. A spa is integrated into the pool with a stone wall feature. Chaises with striped cushions are positioned beside the water, and a spacious patio includes various stone pavers.

Guesthouse in Orlando

4.97 out of 5 average rating, 107 reviews

1926 Spanish Carriage House Lower

Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

Guest favorite

A modern kitchen is showcased with sleek gray cabinets and stainless steel appliances. A spacious island with a granite countertop provides seating for four, while pendant lights illuminate the area. White cabinetry and warm wood flooring enhance the inviting space.

Guesthouse in Sanford

4.95 out of 5 average rating, 164 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 cozy sleeping area is highlighted by two queen-size beds, each adorned with checkered yellow and white blankets. A lamp on a nightstand provides gentle illumination, and natural light filters through the window, which is fitted with blinds.

Guesthouse in Mount Dora

4.96 out of 5 average rating, 258 reviews

Cozy Buttercup Cottage!

Cozy 1/1 cottage- independent building, + nice breakfast kitchen, dining, & living room, great screened porch. 4 minute drive from Renninger’s, 5 minutes from Mount Dora City Hall Area where you'll find unique shops, restaurants, antiques, art museums, galleries, marina, parks, & many activities! *32 min/ Universal Studios & Island of Adventure, 43/ Magic Kingdom, 40 min/ Orlando Intl. Airport, 36 min/ Sanford-Orl Airport, 18 min/ Rock Spring, 48 min/ Silver Glenn Spring & much more!

Top guest favorite

A cozy living area features a blue sofa adorned with patterned cushions. A light wood table and chair provide space for work or relaxation. Two lamps and a flat-screen TV are positioned next to newly installed windows that offer natural light and outdoor views.

Guesthouse in DeLand

4.96 out of 5 average rating, 217 reviews

No Worries Carriage House, 5 min walk to Stetson

This second-floor carriage house is all yours. Located on a quiet street amidst historic homes. Walk to Stetson in 5 min. Downtown DeLand is an easy 15 min. walk. Your two bedrooms, full kitchen, private access will be great for a get-away for you and your guests. 42" flatscreen TV with cable and Amazon Prime with no ads. Wifi. The second-story banks of windows look out over beautiful, tropical plants. Space to work or relax. We look forward to you enjoying your stay with us.

Top 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, 121 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, 118 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!

Guest favorite

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, 157 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 studio space is highlighted by a queen bed, draped in an orange coverlet, and accented by decorative pillows. A small side table holds a basket. A cozy chair sits nearby, and natural light filters through sheer curtains, enhancing the inviting atmosphere.

Guesthouse in Ormond Beach

4.95 out of 5 average rating, 108 reviews

Cozy Guesthouse close to all

Keep it simple at this peaceful and centrally-located place. Just 1.4 miles from the beach and 1 block from Ormond’s pubs and restaurants; you can take a bike or walk to most of the best spots! Designed for ultimate relaxation and equipped with all you’ll need to enjoy your cozy home away from home. We have the beach, the restaurants, and rivers nearby for kayaking or boating! Go one way for beaches and breezy pub crawls and the other for walking paths and lazy river floating.

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, 245 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, 170 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, 146 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