Guesthouse vacation rentals in DeLand

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Top-rated guesthouse rentals in DeLand

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Guest favorite

A cozy outdoor seating area features four Adirondack chairs arranged around a circular fire pit. The space is surrounded by a gravel path and stone pavers, with soft lighting illuminating the scene and a wooden fence providing privacy.

Guesthouse in Sanford

4.94 out of 5 average rating, 147 reviews

Little Hidden Cottage- Near Sanford Airport

Located in Sanford Florida, our Hidden Little Cottage is a private guest house with its own entrance, features a full kitchen and bath room, queen size bed, full size pull out couch and twin size travel bed, and 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 are also central to many Central Florida attractions such as Natural Springs, Sandy Beaches, Theme Parks and Historic Districts.

Top guest favorite

A heated hot tub is nestled within a tranquil pool area, surrounded by lush green tropical plants. A rock waterfall feature flows gently into the pool, enhancing the serene environment. A screened enclosure provides a sense of privacy and protection from the elements.

Guesthouse in Port Orange

4.93 out of 5 average rating, 347 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

Guesthouse in Leesburg

4.98 out of 5 average rating, 385 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

Guest favorite

Clear waters are showcased, revealing a manatee swimming just below the surface. A lone kayaker is seen navigating the water in a green kayak. In the background, a wooden walkway extends through the lush greenery, indicating a natural, serene environment.

Guesthouse in Orange City

4.87 out of 5 average rating, 140 reviews

Moon light Cottage

This cozy spring escape sits privately behind a unoccupied garage among the quiet oak streets of Orange city. conveniently located 2.0 miles from Blue springs state park, 5.0 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! DM me for upgraded garage perks.

Guest favorite

Guesthouse in DeLand

4.97 out of 5 average rating, 103 reviews

The Glass-Flower Cottage

This romantic cottage is perfect for some much-needed relaxation. Your private fenced-in yard has its own outdoor dining area, charcoal grill, paver walkway, and fire chiminea. Nicely located within 2 miles of Historic Downtown Deland, there are numerous unique shops, exquisite eateries, and exciting nightlife nearby. The famous Daytona Beach and Daytona 500 Speedway are 21-25 miles away. Enjoy a cup of coffee and relax a while. Don’t see availability, check out our other places!

Top guest favorite

Guesthouse in Mount Dora

4.96 out of 5 average rating, 251 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 charming two-story house is surrounded by lush greenery and tropical plants. A wide concrete path leads to the welcoming front porch, which features a mix of seating areas and decorative elements. A bright blue sky and sunlight cast a warm glow over the scene.

Guesthouse in DeLand

4.98 out of 5 average rating, 192 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.

Guest favorite

A dedicated workspace is established within the room, featuring a desk with a lamp and a chair. A blue chair is positioned near a small table and decorative plant. Natural light enters through the window, offering a bright and functional area.

Guesthouse in Sanford

4.94 out of 5 average rating, 112 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!

Top guest favorite

Guesthouse in Orlando

5 out of 5 average rating, 247 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

A serene backyard space is illuminated by string lights, creating a warm ambiance. Lush greenery and potted plants are scattered throughout the area. An inviting white Adirondack chair is positioned nearby, providing a comfortable place to relax and enjoy the garden's beauty.

Guesthouse in Lake Helen

4.95 out of 5 average rating, 242 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 favorite

Guesthouse in DeLand

4.9 out of 5 average rating, 458 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

A bright outdoor patio area features a round wooden table with four orange chairs and a large umbrella. Lounge chairs are positioned nearby, and a potted plant adds a touch of greenery. The space is surrounded by well-manicured grass and trees in the background.

Guesthouse in De Leon Springs

4.8 out of 5 average rating, 178 reviews

Relaxing, Private Studio on 6 Acres

Private, relaxing, 550 SQ FT Studio on a 6-acre lot with full kitchen, washer, and dryer. Queen bed, breakfast area, dishware, silverware, cookware, TV, internet, ample closet, and storage space. Located on a scenic route close to all of Central Floridas attractions. 1 Small dog/cat under 20 lbs are allowed with a $50 pet fee. No smoking inside is allowed.