9 Tiny Florida Cottages To Rent for a Warm Winter Escape
The Gardener’s Cottage
Rates starting from $64 per night; Book it!
You might have to hop in the car to get to the beach from this cottage, but the sweet space makes up for it with plenty of other perks, especially for those interested in a more cosmopolitan getaway. Tucked in a National Historic District, it offers easy access to Jacksonville’s lively downtown scene. The studio space is one large room with a bed and small kitchenette, plus an adjoining (private) bathroom.
Key West, Florida
Rates starting from $336 per night; Book it!
This one’s for the lovebirds! Tucked in a light and bright cottage overlooking a pool, this charmingly simple escape features powder blue walls and tropical decor. It’s located just a half-block from Key West’s renowned Duval Street—the perfect distance for a nighttime stroll after a candlelit dinner. The retreat also has a private deck, access to two pools, and complimentary happy hours twice a week.
Santa Rosa Beach, Florida
Rates starting from $50 per night; Book it!
If you’re the outdoorsy type (and are looking for a bargain), this petite cabin is the rental for you. In Santa Rosa Beach, it’s a good pick for anyone who wants to spend all of his or her time lounging on the Gulf coast’s gorgeous beaches or enjoying the nightlife of 30A. The rental itself offers only basic amenities—it’s described as luxury camping—but the setting under a copse of trees is truly lovely—and a reminder that the best escapes are within the great outdoors.
Spanish-Style Guest House
Boca Grande, Florida
Rates average $195 per night; Book it!
Located in Boca Grande on beautiful Gasparilla Island, off of Florida’s Gulf coast, this tiny guest house is just 100 yards from the water and only three blocks from town. The space, just 600 square feet, includes a bedroom with a queen bed, a sitting room, and a bathroom—a simple set-up perfect for a relaxing getaway.
St. Augustine, Florida
Rates starting from $79 per night; Book it!
Those looking for the perfect blend of beach and culture should look no further than this salty escape. The small lodging—which comes with a private porch and outdoor shower, plus access to a shared hot tub and grill—is just 10 minutes from both the nearest beach and St. Augustine’s vibrant Historic Downtown.
Rates starting from $100 per night; Book it!
Surrounded by trees in the laidback Coconut Grove neighborhood of Miami, this secluded spot is serene on the inside and verdant on the outside. Vaulted ceilings give the small space—the cottage consists of a bedroom and a bathroom, plus an efficiency kitchen—an airy feel, while outside dining and lounge spaces offer plenty of room to roam. And while it feels worlds away, the cottage is only 10-15 minutes from South Beach and south Miami, and is very close to the water.
Panama City Beach, Florida
Rates starting from $150 per night; Book it!
Located just 500 feet from the white sand of Laguna Beach, near family favorite Panama City Beach, this private, serene rental boasts colorful, eclectic décor that feels playful and energetic. With slightly more space and amenities than most small cottages (think a full-sized kitchen, washer/dryer, and a living room with a sleeper sofa), Bella Cabana is perfect for families looking for a cozy home base for a weeklong vacation.
North Star Barn
Ponte Vedra Beach, Florida
Rates starting from $70 per night; Book it!
Sure, this one isn’t quite a cottage, but it still offers plenty of charm in a compact space (plus easy access to Ponte Vedra Beach and the Intracoastal). A small apartment is located inside the barn, with a full-size eat-in kitchen and a sitting area. The rental can sleep up to four people comfortably between its queen bed and sleeper sofa—perfect for a family looking for that small-space vibe.
Rates starting from $74 per night; Book it!
What this efficiency cottage lacks in size, it makes up for in style and comfort. Located in Edgewater, Florida, near a river, beaches, shops, and restaurants, this studio cottage (with a privacy curtain dividing the bed from the living area) offers easy access to plenty of outdoor activities, plus use of bicycles, canoes, and beach gear.