Guest house holiday rentals in DeLand

4.98 out of 5 average rating, 413 reviews

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.

Guest house in Leesburg

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

4.95 out of 5 average rating, 102 reviews

A well-manicured pathway leads to the studio, surrounded by lush greenery and colorful plants. Visible are large windows framed by white curtains, providing a view of the scenic lake. A patio with a red umbrella and a picnic table is accessible for outdoor relaxation.

Guest house in Lake Mary

Nature Unique lake view Tiny Guest studio

Tiny Guest house studio with separate entrance for privacy and amazing Lake view. Unlimited rental of 2 Blue kayaks included during stay!! Walking distace from windixie supermarket, downtown lake Mary, restaurants, shopping centers, entertainment and dunking Donuts. Common areas outside studio are shared. Property is at lake Mary across Country club, close to Sanford, Boombah Sports, Orlando Fl. 30 min to Daytona Beach. Near Wekiva springs. To go to Disney, easy access to I-4 and 4-17.

4.94 out of 5 average rating, 175 reviews

Guest house in Sanford

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

4.93 out of 5 average rating, 123 reviews

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.

Guest house in Sanford

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 house in Orange City

A cozy seating area features a teal sofa adorned with two decorative pillows. Above, shelves are filled with books and decorative items. A small lamp illuminates the space, while a window offers a view of the outdoors, complemented by a nearby mini fridge.

4.85 out of 5 average rating, 164 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!

Guest house in Ormond Beach

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.

4.96 out of 5 average rating, 117 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.

Guest house in Lake Eola Heights

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.

5 out of 5 average rating, 265 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!

4.87 out of 5 average rating, 207 reviews

A spacious bed is positioned against a light blue wall, complemented by mirrored accents on the headboard. Two lamps are placed on mirrored nightstands, and decorative wall mirrors above the bed enhance the room's brightness. Flowing gray curtains frame a large window, allowing natural light.

Guest house in Bentwood

Chic & Cozy Modern Pool Home

Escape the crowds and relax in this fully private 1BR guest house just 10 minutes from the beach and 15 minutes from Daytona. Located in a quiet, safe neighborhood, this newly renovated pool home features a full kitchen, walk-in closet, sleeper sofa, and access to a shared pool, outdoor shower, and half bath. Ideal for those that want to enjoy all Daytona has to offer, but prefer to get some peace and quiet!

Guest house in Lake Helen

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.

4.95 out of 5 average rating, 248 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.

Guest house in De Leon Springs

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.

4.93 out of 5 average rating, 150 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

4.9 out of 5 average rating, 502 reviews

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.

Guest house in DeLand

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 house in Lake Helen

The living area contains a comfortable seating arrangement with a spacious couch and two armchairs. Natural light floods in through multiple windows, and a light rug sits under a small coffee table. A fan is positioned above for airflow, enhancing the inviting ambiance.

4.95 out of 5 average rating, 100 reviews

Lake Helen Getaway

Keep it simple at this peaceful and centrally-located studio less than a mile off of I4 in a quiet equestrian, golf cart community. Close to shopping/restaurants, Stetson University, historic downtown Deland, Blue Springs, DeLeon Springs, Cassadaga spiritualist community, Daytona Beach, New Smyrna Beach, and only 48mi from Disney/38mi Universal Studios.

Popular amenities for guest house rentals in DeLand

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

The front porch features two wicker chairs with bright orange cushions, inviting relaxation. Potted plants and hanging baskets add greenery, while a gentle overhang provides shade. A pathway leads to the entrance and a nearby guest house, framed by well-maintained shrubs.

4.97 out of 5 average rating, 353 reviews

Oasis Garden Cottage -cozy, chic, near everything!

A spacious suite is displayed with light blue walls and a full bed featuring striped bedding. A smart TV is mounted on the wall, while a small kitchenette with a refrigerator and a dining area is visible. Natural light enters through a window shaded with blinds.

4.93 out of 5 average rating, 252 reviews

"Modern Suite"

An open space features a cozy sleeping area with a patterned quilt atop a spacious bed. A glass dining table with two modern chairs is positioned in the foreground, accented by a decorative vase. Light-colored tile flooring enhances the room's brightness.

4.96 out of 5 average rating, 214 reviews

Welcome to The Blue House

A light blue elevated guesthouse features a spacious deck with white railings overlooking a landscaped yard. A set of stairs leads up to the entrance, surrounded by greenery and large trees. The ground area includes outdoor seating, complementing the serene environment.

4.98 out of 5 average rating, 243 reviews

The Loft in College Park

Guest house in Fort McCoy

An outdoor shower is framed by rustic wooden panels, providing privacy while being surrounded by natural scenery. A grassy area and trees are visible in the background, enhancing the serene atmosphere of the space, suitable for refreshing outdoor experiences.

4.88 out of 5 average rating, 289 reviews

Blueberry Farm Country Cottage

4.95 out of 5 average rating, 197 reviews

A well-equipped kitchen is visible, featuring modern cabinetry and stainless steel appliances. A small dining table is positioned in the foreground, adorned with a vase of fresh flowers. The backsplash adds a touch of elegance, complementing the overall clean and bright design.

Guest house in Clermont

Modern efficiency ~ Great location

Guest house in Thornton Park

A charming exterior of a cottage-style house is framed by lush greenery and well-kept landscaping. A friendly Golden Retriever stands on the front lawn, which features a mix of plants and decorative elements. A welcoming porch with seating is visible, inviting relaxation.

4.9 out of 5 average rating, 781 reviews

Thornton Park's Historic Guest House - private

An outdoor pool is centered within a landscaped patio area, surrounded by lush greenery and mature plants. Two teak lounge chairs are positioned in the foreground, facing the calm water, while sun umbrellas and vibrant seating are visible nearby.

4.89 out of 5 average rating, 157 reviews

Vintage Florida Vibes House

Guest house rentals with a patio

Guest house in Winter Garden

A welcoming outdoor space is presented with two patterned armchairs and a wicker chair arranged around a glass-topped table. A decorative wall feature adds texture, while potted plants and a decorative heron enhance the tranquil atmosphere. Warm light filters through the area.

4.93 out of 5 average rating, 100 reviews

Blue Heron Bungalow

Guest house in Titusville

A well-maintained exterior area features a large leafy tree providing shade. The guesthouse is visible with a light-colored facade and welcoming entrance framed by potted plants. A wooden structure is situated nearby, contributing to the private and tranquil atmosphere of the outdoor space.

4.99 out of 5 average rating, 147 reviews

Rocket City Retreat Titusville Space Coast

A charming arched bridge is framed by lush greenery and hanging Spanish moss. The surroundings are filled with trees and plants, creating a serene outdoor space that invites exploration.

4.93 out of 5 average rating, 179 reviews

Jefferson St. Cottage

The exterior of the property is framed by a vibrant tropical garden, featuring lush greenery and colorful plants. A stone pathway leads to the entrance of the house, bordered by well-maintained grass and large trees, creating a welcoming approach.

4.89 out of 5 average rating, 160 reviews

The Little House

4.97 out of 5 average rating, 176 reviews

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.

Guest house in Maitland

Private 1-bd Mid-Century Guesthouse

Guest house in Delaney Park

A bedroom features a spacious bed dressed in white linens, positioned against a striking black wall adorned with abstract patterns. Natural light is allowed in through an adjacent door, while decorative elements, including wall art and a plant, add a touch of character.

4.96 out of 5 average rating, 320 reviews

Private Guest Suite in heart of Downtown Orlando

Guest house in Lake Cherokee

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.

4.97 out of 5 average rating, 117 reviews

1924 Spanish Carriage House Lower

A charming entrance showcases a white door adorned with a circular floral wreath reading 'welcome.' Flanking the door are two planters with lush greenery, and the address '114 GH' is displayed above the door under an awning.

5 out of 5 average rating, 226 reviews

The Sacred Space Downtown Orlando Milk District

Guest house rentals with a washing machine and dryer

Superhost

A spacious outdoor area features a fire pit surrounded by seating options, including loungers and umbrellas. Lush greenery adds a natural backdrop, and the setting is illuminated by a warm evening glow, creating a welcoming environment for relaxation.

Guest house in Wadeview Park

4.85 out of 5 average rating, 107 reviews

Relaxing Private Studio in the Trees!

The exterior of the two-story cottage is captured, showcasing a red and white color scheme with black shutters. Lush green landscaping and a well-maintained lawn surround the home, while a concrete driveway leads to a detached garage nearby. A white picket fence adds charm to the property.

4.91 out of 5 average rating, 185 reviews

8th Green Cottage - A relaxing oasis in the city

4.99 out of 5 average rating, 140 reviews

Top 1% ABNB Villa Oasis w/ Botanical Courtyard

The studio features a spacious queen size bed with a warm throw blanket, paired with nightstands on either side. A dining area with high chairs is visible near a modern kitchen, which includes stainless steel appliances. A ceiling fan and artwork enhance the stylish decor.

4.96 out of 5 average rating, 135 reviews

Modern 1950s Studio • Near Downtown & Theme Parks

A living area is presented with a comfortable gray sofa adorned with decorative pillows. A white coffee table is centered in front, accompanied by a minimalist glass side table. Tall plants bring a touch of greenery, while a television completes the space.

4.92 out of 5 average rating, 130 reviews

Kyle's Place - Private Unit, Pool + Laundry Room

Guest house in Wadeview Park

A spacious bedroom features a large bed with white bedding and decorative pillows. Two soft bedside lamps illuminate the area, complemented by a cozy armchair and a decorative bench at the foot of the bed. Exposed brick wall accents the room.

4.98 out of 5 average rating, 118 reviews

The Cottage A Pet Friendly Guesthouse

A comfortable living area features a dark leather sofa, a wooden coffee table, and a dining table with chairs. Bright light filters in from the outdoor patio, revealing lush greenery and a seating area beyond the sliding glass doors adorned with a vibrant red umbrella.

4.96 out of 5 average rating, 458 reviews

The Coach House -2 bedroom/3 bath Orlando Getaway!

A comfortable living area is furnished with a dark sofa and an armchair. A light-colored throw blanket is draped over the sofa, and a patterned area rug adds warmth to the tiled floor. Natural light streams through the windows, illuminating the dining area in the background.