Guest house holiday rentals in Florida

Hot Tub + Outdoor Theater + Free Wine! + Ping Pong

You will Experience serenity at The Loft House Retreat! Amidst lush Florida plants, unwind in a hot tub, challenge friends to ping pong, or cozy up by the fire pit and Projector. Inside, enjoy 2 full beds & refresh in a full bathroom with a walk in Shower. Explore Tampa's gems: Busch Gardens, Downtown Tampa, Waterstreet, Armature Works, Zoo Tampa, The Florida Aquarium, Raymond James Stadium, Sparksman Wharf, Michelin-starred restaurants, and historic eateries. Book your unforgettable escape now!

The Cocoa Boho Rooftop Retreat

Escape to your own slice of paradise, a brand-new boho-chic retreat just 2 minutes from the beach! Picture this: ocean views from your private rooftop patio, mimosas in hand, Atlantic breezes flowing through bright, airy interiors. This isn't just accommodation, it's your perfect beach escape. Whether you're planning an unforgettable girls' trip, a romantic poolside retreat, or the ultimate theme park + beach combo vacation, Cocoa Boho delivers that perfect coastal vibe you've been craving.

"Luxury Casita/Jacuzzi/Bush Gardens/USF/Casino"

Private townhouse style unit with its own entrance, parking, patio, and outdoor amenities. Attached to another Airbnb unit but completely separate with its own entrance and outdoor space. Enjoy this modern Tampa getaway with jacuzzi, pergola and putting green. Minutes from Busch Gardens, USF, and Seminole Hard Rock Casino. Features a modern kitchen, Smart TVs, Wi-Fi, and outdoor space. No parties, events, gatherings, or loud music permitted. Please respect quiet hours and neighboring guests.

Key West Style Suite with Pool/Spa

This beautiful Key West Style studio with kitchen and WIFI is located in the historic neighborhood of Flamingo Park. It’s close to restaurants, downtown Rosemary Square, the Norton Art Museum, the WPB Convention Center, the Palm Beach International Airport, the instracoastal waterway and 5-10 minUte drive to Worth Avenue in Palm Beach and the Palm Beaches. We welcome couples, solo adventurers and business travelers who can enjoy a private backyard guest suite with salt water pool and spa.

The Bunkie on Wetappo Creek

Enjoy a tranquil getaway in this cozy and comfortable studio cottage overlooking the water. Are you working remotely and looking for the perfect retreat space? A couple looking to leave it all behind for a bit and recharge? Come and enjoy the peaceful sounds of happy birds and whispering pines, all while being a short 15 minute drive away from the Gulf of Mexico and its white sand beaches. This private and peaceful space surrounded by Mother Nature invites you to relax and unwind.

Loft Apartment/studio/kitchenette /porch

3 Miles from I75 exit 414 .studio apartment w/ porch over barn. Fire pit with wood available. Grill. Hammock swings under oaks. Stalls available. Close to riding/hiking trails in O'leno State Park. Close to springs for tubing/kayak/canoe. Ichetucknee Spring State Park, Ginny Springs, ++. Also 15 minutes from Santa Fe River and paddling/kayak/canoe rentals . Diving excursions available in High Springs. Quiet setting w/ pastures and grand daddy oaks.

Extraordinary location, private, beach path, cozy

Location, privacy, ocean. Due to health concerns, pool seen from aerial shots not available Nov-May because owners will be in residence in the main house. Welcome to Nova Beach Cottage, the guest house on the oceanfront estate of famous sculptor, Mihai Popa, a.k.a. “Nova”. Located on the south tip of North Hutchinson Island directly next to the Fort Pierce Inlet State Park. Garden and beach path a few steps from the cottage. Screened patio from bedroom.

Stylish Private Studio | Walk to UF

NEWLY RENOVATED | WALK TO UF | PRIVATE STUDIO Stay in a stylish mid-century modern studio just 0.5 miles from the University of Florida—perfect for game days, campus visits, and graduations. Located 2 miles from UF Health Shands and HCA hospitals, ideal for medical stays. This private, detached guest house features modern finishes, natural light, a kitchenette, mini fridge, Smart TV, fast WiFi, and workspace. Quiet, central location near UF and downtown.

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!

Villa Samsara - on a beautiful 5 acre farm

When you come and stay with us, it’s a deeply immersive experience with our horses. Often you will find them in your front door or window. There is something profoundly impactful about being around horses and sharing close-quarters with them. You are in their energy field, receiving all that they have to offer. Without even realizing it, your energies are being grounded and regulated through their presence.

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area has to offer. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.

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.