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Cottage holiday rentals in Florida

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Top-rated cottage rentals in Florida

Guests agree: these cottages are highly rated for location, cleanliness and more.

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Cottage in Cudjoe Key

4.91 out of 5 average rating, 133 reviews

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

3–10 Mar

$1,209 SGD per night

Cottage in Hawthorne

4.86 out of 5 average rating, 111 reviews

Live Oak Oasis on Morris Lake

Unspoiled nature greets your every turn at this charming 650 SF lakefront retreat. A short distance from 10 of Florida's finest 1st magnitude springs, ranging from 30 - 90 minute drive, makes the location a perfect basecamp for adventure travel. Rest beneath the shade of Live oaks that pull the breeze ashore. Enjoy Sand hill cranes and hummingbirds from the cabana. Incredible sunsets from new dock. Paddle boat & paddle boards available for adventures. WiFi, Netflix, Laundry, HOT outdoor shower!

24 Sep – 1 Oct

$128 SGD per night

Guest favourite

Cottage in Key Largo

4.96 out of 5 average rating, 146 reviews

Charming Key Largo Cottage on the Water w/Kayaks!

Charming "Tiny House" Cottage on a main canal just two units from open water. Amazing location for boaters, fisherman and alike. This is a quaint and close knit RV park where you can keep to yourself or wander around and enjoy happy hour with new local friends. Bar none the best kayak, paddle board and fishing area. Two Tandem (each kayak accommodates two people) Kayaks and two paddle boards included in rental. Great outdoor space to dock your boat, fish off of or enjoy a few cocktails!

2–9 Oct

$498 SGD per night

Cottage in Islamorada

4.85 out of 5 average rating, 128 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

7–14 Sep

$243 SGD per night

Guest favourite

Cottage in Panama City Beach

5.0 out of 5 average rating, 106 reviews

NEW cozy beach cottage 3 blocks from beach!

Welcome to your home away from home! Our fully renovated & modern beach cottage is the perfect place to relax & reset, whether that's lounging in our bright, cozy living room, spending the day at the beach (a quick 3 block walk) or sipping on your drink of choice by the fire pit in the backyard. We are centrally located between 30a & Pier Park with plenty of amazing restaurants, shops & nightlife to experience. Come stay with us, we're always open! Follow us on IG @its.alwaysopen

3–10 Jul

$477 SGD per night

Cottage in St. Augustine

4.91 out of 5 average rating, 107 reviews

The Shire on 1 acre marshfront with dock and Spa

One of a kind 1930s historic home, newly renovated and transformed into a beautiful secluded getaway. new luxury finishes, while holding its traditional charm. No Events allowed. Rooftop deck, sunrise views of the Atlantic ocean, Downtown, and sunsets over the river. The new dock with covered roof hosts a national geographic like eco system. It’s short walk to the beach and 3 miles to downtown St George street. Follow along @carcabaroad for weekly content of the home.

1–8 May

$561 SGD per night

Cottage in Santa Rosa Beach

4.95 out of 5 average rating, 150 reviews

Vibe: Coastal living experience. Screened pool.

Want a true coastal experience? Vibe isn’t just another stale beach rental. It's a coastal living experience! Vibe's designer-renovation features hand-cut shiplap ceilings and local artisan hand-painted furnishings create a beach cottage feel that warms the soul. Take the free included 6 seater golf cart through Vibe's charming neighborhood to the sugar sand beach in under 3 minutes. Then return home to relax in your private screened seasonally heated pool and hot-tub.

24 Feb – 3 Mar

$1,322 SGD per night

Guest favourite

Cottage in Davenport

4.92 out of 5 average rating, 129 reviews

$79! Cozy Cottage + Outdoor Fun -Close to Disney!

Book with us now and receive access to all of these amenities✨: •Lightning Fast Internet ⚡️ •Outdoor Movie Theater 🎥 •Ping Ping Table/Pool Table 🏓🎱 •Complimentary Coffee & Breakfast ☕️ •Safe Gated Location •Large Enclosed Covered Patio •Comfortable Queen Sized Bed •Cable TV (Adjustable) •Modernized Brand New Full Bathroom •Nearby All Major Attractions •Outdoor Dining Area •Kitchen, Fridge/Freezer, & Breakfast Nook •And Much More! Book with us now!

10–17 Jul

$132 SGD per night

Guest favourite

Cottage in Bradenton Beach

4.99 out of 5 average rating, 124 reviews

Bradenton Beach Sunsets 2, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

26 Nov – 3 Dec

$319 SGD per night

Cottage in Kissimmee

4.83 out of 5 average rating, 218 reviews

Private Cottage. Only 5 miles from Disney.

Welcome to our private cottage on a 4 star resort only 5 miles from Disney World in Kissimmee, Florida. This home has some smart home features such as Alexa, smart thermostat that Alexa can control. It has a smart lock that makes it convenient for you when you stay your are given a confidential code for your stay only. The cottage is a one bedroom one bathroom with a queen size bed. Also the sectional couch turns into a full size bed.

22–29 Jan

$130 SGD per night

Guest favourite

Cottage in Kissimmee

4.94 out of 5 average rating, 402 reviews

Entire cottage for 5, close to Disney, Universal!

Great cottage for 5, come stay! One bedroom with a adjustable com-fee queen bed, and a 19" flat screen TV. Loft 1 queen, 1 twin, don't bump your head. Located only minutes from Disney and Universal. Heated pool! Our place is completely updated, new furniture , appliances etc. we also have on property three other cottages Bitty Bungalow. Bitty Bliss, and the Bitty blossom. All are Smoke free, pet free.

13–20 Nov

$124 SGD per night

Guest favourite

Cottage in Destin

4.94 out of 5 average rating, 241 reviews

Two blocks to the beach! Bikes included!

Newly remodeled ⭐️Private beach bungalow in Crystal Beach! ⭐️This property is a private guest house two blocks from the beach! You will have your own entrance and parking for one car. Downstairs you will find living area, full kitchen, washer/dryer, and bathroom. The loft has 2 queen beds. Small courtyard for outdoor seating & outdoor shower. Wonderful neighborhood with sidewalks for biking or walking!

16–23 Jan

$290 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Chalets

Adventure-ready homes with après-ski style

Bungalows

Intimate homes, inviting architecture

Popular amenities for cottage rentals in Florida

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Guest favourite

Cottage in Kissimmee

4.98 out of 5 average rating, 140 reviews

Runaway Beach Resort Pet Friendly: Magic Kingdom

20–27 Apr

$198 SGD per night

Guest favourite

Cottage in Port St. Joe

4.98 out of 5 average rating, 121 reviews

2 mins to beach, Poolside + Hot Tub, Fully Stocked

21–28 Feb

$271 SGD per night

Guest favourite

Cottage in Anna Maria

4.98 out of 5 average rating, 208 reviews

Turtle Cottage - Anna Maria Island

22–29 Dec

$795 SGD per night

Guest favourite

Cottage in Orlando

4.97 out of 5 average rating, 103 reviews

Lake House

17–24 Feb

$324 SGD per night

Guest favourite

Cottage in Monticello

4.96 out of 5 average rating, 112 reviews

The Cottage at Grand Oaks Plantation

7–14 Dec

$359 SGD per night

Guest favourite

Cottage in Kissimmee

4.81 out of 5 average rating, 142 reviews

Cozy cottage close to Theme parks and shopping.

4–11 Apr

$156 SGD per night

Guest favourite

Cottage in Weeki Wachee

4.96 out of 5 average rating, 162 reviews

Coastal Cottage Getaway

24–31 Mar

$160 SGD per night

Cottage in Keystone Heights

4.84 out of 5 average rating, 193 reviews

"Love Shack"

20–27 May

$144 SGD per night

Pet-friendly cottage rentals

Guest favourite

Cottage in Pensacola

4.99 out of 5 average rating, 111 reviews

Perdido Coastal Cottage-4 min beach/golf-Pets Ok!

13–20 Sep

$246 SGD per night

Guest favourite

Cottage in Little Torch Key

4.91 out of 5 average rating, 146 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

27 Apr – 4 May

$752 SGD per night

Guest favourite

Cottage in West Palm Beach

4.93 out of 5 average rating, 217 reviews

Tangerine Dream at The Citrus Cottage, heated pool

6–13 Oct

$406 SGD per night

Guest favourite

Cottage in West Palm Beach

4.96 out of 5 average rating, 254 reviews

Downtown Cottage-Quiet-Private-Close to Everything

20–27 Aug

$156 SGD per night

Cottage in Astor

4.83 out of 5 average rating, 326 reviews

St John's Cottage Astor- escape to the forest!

14–21 Sep

$93 SGD per night

Guest favourite

Cottage in Pensacola

4.98 out of 5 average rating, 421 reviews

Eclectic Eco- Friendly Luxe City Cottage

26 Nov – 3 Dec

$203 SGD per night

Guest favourite

Cottage in St. Augustine

4.92 out of 5 average rating, 185 reviews

Bluefish Bungalow, Funky Little Beach House

8–15 Aug

$279 SGD per night

Guest favourite

Cottage in Dunnellon

4.96 out of 5 average rating, 162 reviews

Cozy Cottage. Surrounded by nature, not neighbors.

21–28 Jun

$174 SGD per night

Private cottage rentals

Guest favourite

Cottage in Santa Rosa Beach

4.98 out of 5 average rating, 174 reviews

Beach Cottage South of 30a -Steps to Beach & More!

20–27 Mar

$602 SGD per night

Guest favourite

Cottage in Panama City Beach

4.96 out of 5 average rating, 117 reviews

Beach Cottage at the Heart of the Best of 30A

30 Jan – 6 Feb

$513 SGD per night

Guest favourite

Cottage in Santa Rosa Beach

4.96 out of 5 average rating, 106 reviews

Summer! Public beach-easy beach access, bikes!

11–18 Feb

$423 SGD per night

Guest favourite

Cottage in Kissimmee

4.86 out of 5 average rating, 395 reviews

Yay! Cool Tiny Home Near All the Parks (98)

15–22 Jan

$129 SGD per night

Cottage in Port St. Joe

4.85 out of 5 average rating, 124 reviews

Sun Kissed Cottage on the beach

8–15 Oct

$407 SGD per night

Cottage in Naples

4.9 out of 5 average rating, 190 reviews

The LUV Shack! · Close to Beaches·Dining·Shopping

16–23 Jun

$234 SGD per night

Cottage in Sarasota

4.83 out of 5 average rating, 150 reviews

Charming Beach Cottage

9–16 Nov

$219 SGD per night

Guest favourite

Cottage in Cocoa

4.95 out of 5 average rating, 128 reviews

Coconut Cottage-Cruise Ports, Beaches, & Launches!

27 Feb – 6 Mar

$309 SGD per night

Destinations to explore