What is it about having your own four walls when you’re on vacation? Besides being free from hearing mysterious noises (or worse, recognizable ones…) on the other side of the wall? Is it the simplicity of carrying your few belongings through the door, arranging them in a small dwelling that someone else thoughtfully decorated and put fresh sheets on your bed? Or does having one’s own bungalow hearken back to worry-free childhood, that playhouse where you pretended to be a grown up and served tea?
As travelers we all are seeking to shed parts of our daily life, whether it be the constant upkeep of our homes, the sometimes plodding day job, financial pressures, health concerns, or worrying we’re too old for skinny jeans. (I overheard that recently, seems fitting to include it.) Living small – or at least spending time in a small vacation cottage – frees and clears our minds.
Sunset Inn, Treasure Island, MacDill Cottage
The small house and tiny house movements are big for a reason. Maybe we’re not quite ready to throw out and donate all the accumulated junk we no longer need, but we can pretend, in our little ‘own four walls’ that we’re actually capable of living this way. And we will. As soon as we get back home, we’ll begin. But for now, the beach is calling…
In Florida we have a bounty of vintage motel properties that have been cleverly renovated, keeping all the best parts of their olden-days charm and adding levels of modern comfort we all seek.
85 Defuniak St.
Grayton Beach, FL 32459
With three distinctive buildings, the historic Hibiscus Coffee and Guesthouse offers multiple types of lodging including some that are pet-friendly, kid-friendly and have wheelchair access. Two rooms have full kitchens, two others share a kitchen, and the rest include mini fridges, microwaves and coffee pots. Click their name above to visit their site and choose the accommodation that best suits you.
Bert’s Barn was built in 1905 and houses 5 guest rooms, the cafe building is also home to 4 original guest rooms, and the office building includes 3 luxury suites. What captured our attention is their Woodpecker Cottage, an adorable freestanding private oasis with a queen bed, a small living area and its own screened porch.
- RATES: Approximately $165 depending on the time of year. A two night minimum is required on weekends.
- WALK: The gorgeous white sandy beach and most shops and restaurants – including the famous Red Bar – are an easy half mile walk along quiet shady streets.
- PETS: Check the website for which rooms allow pets; the Woodpecker Cottage is not one of them.
2105 Highway 98
Mexico Beach, FL 32410
The Inn itself sits directly on the beach, as do the Cottages, which are duplexes and triplexes. The Victorian Houses (one is shown above) are directly across the street. The Victorian Houses are stand-alone and have 2 bedrooms, full kitchens, dining and living rooms with plank wood walls and hardwood floors.
- RATES: The beauty of The Driftwood is the Cottage rooms and the main Inn rooms have the same rate, $110 – 150/night depending on the season. The Victorian Houses are just a little more at $130 – 185. A two night minimum is required on weekends, and a 3 night minimum on holidays.
- WALK: The beach is a short walk across the street from the Victorian Houses, and a number of great restaurants are within a half mile including Toucan’s to the south, and Mango Marley’s to the north.
- PETS: Pets are welcome at the Driftwood Inn, check the website for fees.
PORT ST. JOE
314 Cecil G. Costin Sr. Blvd.
Port St. Joe, FL 32456
Partners with the historic Port Inn, the Port Cottages are new vacation rental homes with many amenities. Each cottage has 2 bedrooms, 1.5 baths, 3 flat screen tv’s, fully stocked kitchen, full size washer and dryer, private pool, grills, and extended parking for boat trailers. Port Cottage guests also have access to all Port Inn amenities including a heated pool, bikes, and The Thirsty Goat Lounge (you know you want to check it out, with a name like that!)
- RATES: With all they offer, the rates of $209-279, depending on the season, are reasonable.
- WALK: Multiple gourmet and casual restaurants are within walking distance, and The Thirsty Goat is just around the corner. The lovely bayfront is also right there, and Mexico Beach is 12 miles to the north, Cape San Blas beach 12 miles to the south.
- PETS: Pets are welcome in all Port Cottages, check with the owners for fees.
322 Riverside Dr.
Steinhatchee, FL 32359
Speaking of names that capture our imaginations, Sea Hagg Shacks sounded brilliant even before we saw how colorful and fun they are. With over 20 shacks to choose from, with a range of either 1, 2, 3, 4 or 6 bedrooms, and a variety of amenities (some have central heating and air, other window unit a/c, some have gas grill cook sheds; click their name above for a detailed list and charming photos) we predict you’ll happily spend awhile on their site. Each shack has a fish/seafaring name, including our favorite, Scallywag, the definition of which is “A person who behaves badly but in an amusingly mischievous rather than harmful way” (sounds like some of our closest friends!)
- RATES: The one bedroom Shrimp Shack ranges from $60-129 depending on the season, while the 6 bedroom Scallywag Shack is $199-349.
- WALK: Steinhatchee is not a beach town but a fishing, scalloping town. Restaurants like Roy’s are 1/2 mile away, and Fiddler’s is 1 mile away.
- PETS: Pets are not allowed.
847 3rd St.
Cedar Key, FL 32625
Hurricane Hermine tore through Cedar Key last September devastating many businesses and resident’s property. Reading the stories again while doing research for this article still brings goosebumps to my arms; how horrific that day was. But with strong determination and brave visions for their rebuilt future, the town, with so much help from volunteers arriving from all over, Cedar Key is back and welcoming all of us. One of our favorite towns ever (one of the few we’ve thought of moving to someday!) Cedar Key is a must-visit for Florida travelers. Read details here, and visit Faraway Inn’s website (click their name above) to choose your charming bungalow.
- RATES: Cottages are $150 with 2-4 night minimums during festivals, holidays and peak season. Motel rooms are $90 – even if a cottage doesn’t fit your budget, the motel rooms are just as charming.
- WALK: Walk everywhere in Cedar Key; the water is just across the street, the lovely historic downtown is a 4 minute walk and Dock Street, with multiple fun restaurants and shops and gorgeous views of the Gulf is a half mile away.
- PETS: Faraway Inn is one of the most pet-friendly places we’ve ever encountered, with pet washing and grooming stations, pet treats and towels, six poop-pick-up bag stations, no size restrictions (good behavior is a must.) Companion animals such as cats and birds are welcome, and they’ve also had lizards and hamsters as well!
10606 Halls River Rd.
Homosassa, FL 34448
Homosassa River Retreat is a true fish camp – except some of the cottages are PINK. Which we love. And the fishermen who stay here must, too. Rustic yet comfortable, a compound of cottages under the trees, with the above cottage – The Bait House – on the water. Seven 1 bedroom cottages and two 2 bedroom cottages are available, and all have fully equipped kitchens, A/C and cable television.
- RATES: The lowest priced cottage – The Dinghy – is $80, The Bait House is $120. There is a two night minimum on weekends and three nights on holidays.
- WALK: The charming downtown area of Homossasa is across the river (and a short drive away) but the waterfront Seagrass Pub and Grill is just down the street.
- PETS: Pets are welcome at the Homossasa River Retreat, check with the owner for fees.
7925 W. Gulf Blvd.
Treasure Island, FL 33706
For the Triple B Team to ever say “THIS place is our favorite”… well, that would be like a parent choosing his favorite child and telling each one who it is. But we will confess to having a Top Ten, and Sunset Inn is on this list. Located on Sunset Beach in Treasure Island, Sunset Inn was transformed when two young women took an old, run-down hotel and through much planning, creativity and elbow grease (Mom used that term a lot; there is no better way to describe it) created this colorful retreat. The Before and Afters are amazing, as is their story, read about it here: They Dared to Dream. Also read a fun article with cool photos and lots more detail, Sunset Beach, Florida: A Welcome Oasis Just a Stroll Away From the Madding Crowd. From hotel rooms to individual cottages, Sunset Inn offers perfect old-Florida charm with modern amenities. There are minimum night stays required.
- RATES: Rates are seasonal, click their name above to search for rates and room types. For example, in September the Vino Cottage (a 1/1) is $225, and an Inn room is $140.
- WALK: The beauty of Sunset Inn is it is located in a quiet, mostly residential area just across the street from the beach. Within walking distance is the famous Caddy’s on the Beach and many shops and restaurants are a short drive away.
- PETS: Some cottages are pet friendly, check the website.
ANNA MARIA ISLAND/BRADENTON BEACH
2000 Gulf Dr. North
Bradenton Beach, FL 34217
With some bungalows directly on the Gulf of Mexico, others facing the pool or lovely courtyard – one, two and three bedroom bungalows – Bungalow Beach Resort offers accommodations for any size family. Built in the 1930’s and fully updated, the cozy resort is nestled in its own private and beautifully landscaped tropical paradise. Each bungalow (I love saying that word) has either a mini-bar kitchenette, efficiency, full or gourmet kitchen with a microwave. Holidays, weekends and special events are subject to special rates and minimum stays.
- RATES: Bungalows start at $239 in the summer months.
- WALK: Several restaurants are within walking distance, and the charming downtown Bradenton Beach is a little over a half mile away.
- PETS: Pets are not allowed.
6351 Gulf of Mexico Dr.
Longboat Key, FL 34228
“Your own little house on the beach!” their website cheerfully states. Old-Florida meets updated comforts at Rolling Waves seven 1 bedroom cottages and one 2 bedroom cottage. Each cottage has a fully equipped kitchen with refrigerator, conventional and microwave ovens, coffee maker and toaster. A four night minimum is required.
- RATES: Fall/winter rates start at $175 and spring is $265, with the beachfront cottages $195-325.
- WALK: A number of restaurants are within about a mile in either direction, and the vibrant shopping/dining area, St. Armand’s Circle, is 10 miles to the south.
- PETS: Pets are welcome at Rolling Waves Cottages, check the site for fees.
4760 Pine Island Rd.
Matlacha, FL 33993
Located in the historic district of Matlacha – one of Florida’s most colorful, creative little towns – Matlacha Cottages offers three units with kitchens, A/C and heating, cable television, Wi-Fi, parking, private decks and dock and a stunning waterfront view of Matlacha Bay. The minimum stay is two nights.
- RATES: From $114 -175 depending on the unit and the season. Click on their name above for more details.
- WALK: Matlacha Cottages are within easy walking distance of all that Matlacha has to offer: shops, restaurants, art galleries, kayaking, fishing, birding, boating.
- PETS: Pets are not allowed.
15107 Captiva Dr.
Captiva Island, FL 33924
A cozy shaded enclave of historic cottages is gathered along a path that leads down to the water, Jensen’s Marina, and tiki huts for your use. The vibe here is about the kind of relaxation found in simpler days. Jensen’s offers studio cottages, one bedroom suites, one bedroom cottages and two bedroom cottages with either one bath or two. Jensen’s also has a beach front resort. A minimum stay may be required, click on their name above for more info.
- RATES: Approximately $160 and up, depending on the cottage and the season.
- WALK: Jensen’s is within walking distance of all the fun restaurants, shops, and the beach.
- PETS: Pets are not allowed.
The Cottage Capital of the World, Sanibel Island deserves its own article, which we will be writing soon. In the meantime, click on the sites below to visit these updated old-Florida treasures.
1180 Edington Place
Marco Island, FL 34145
The Boat House Motel is located on the northern tip of Marco Island in a quiet, charming area dubbed “Olde Marco.” Family owned and operated since 1994, The Boat House offers traditional motel rooms and the Gazebo House, pictured above. With amazing water views and a wraparound deck, the Gazebo house is a two bedroom two bath private bungalow with a full kitchen and televisions in every room. Make sure to book early as this lodging is very popular! A four night minimum is required.
- RATES: Contact the Motel by clicking their name above or call directly.
- WALK: The Boat House Motel is within a short walk of great restaurants and shops. The beach is approximately 3 miles away.
- PETS: Pets are welcome, check with the owners for fees.
2435 S. Atlantic Ave.
Daytona Beach Shores, FL 32118
Shoreline All Suites Inn & Cabana Colony Cottages is located in quiet Daytona Beach Shores directly on the ocean and offers suites plus quaint private cottages, a heated oceanfront pool and of course the beach itself. All cottages have fully equipped kitchens with the exception of the smallest – they call it their mother-in-law suite – that does have a mini fridge. This cottage is very budget-friendly and with all the restaurants in Daytona Beach Shores and Daytona Beach you won’t go hungry. There are minimum night requirements.
- RATES: Starting at just a little over $100 a night for the small no-kitchen cottage, rates are slightly higher for the cottages with kitchens and of course for the ocean view cottages; click their name above to visit their site and view rates.
- WALK: There are a couple of restaurants within walking distance and many just a short drive away.
- PETS: Pets are welcome in the cottages for an additional fee.
11330 U.S. 1
Sebastian, FL 32958
Situated close to the Indian River and ten minutes to the beach, Pelican Island Cottages offer a quiet (and so cute – those colors!) vintage Florida experience with clean and cozy interiors. Repeat visitors come to go kayaking, boating, fishing and surfing. Choose from 1 bedroom or 2 bedroom cottages with full efficiency kitchens with all the basic supplies. Wi-Fi on the property as well as a “Game Cottage” with a pool table and big screen t.v. where guests can gather. Click their name above for a full list of accommodations and amenities.
- RATES: Starting at $129 in the Winter (December 15 through April 20) and $90 in the Summer (April 21 through December 14.)
- WALK: Many waterfront restaurants are within walking or biking distance, read “Where Else in Small Town Florida Can You Stay in a Pink Cottage and Walk to 10 Waterfront Restaurants?”
- PETS: Non-barkers are welcome with some restrictions, read more on their site.
1312 S. Ocean Dr.
Vero Beach, FL 32963
Photo courtesy of Seahorse Beach Cottages
Located in a peaceful residential area, Seahorse Beach Cottages are a best-kept secret directly on a quiet, mostly uninhabited beach. Each of the one bedroom and two bedroom cottages has a separate living room, kitchen, bedroom and bath. Private decks, gas BBQ grills and fully equipped kitchens are just some of the amenities, click on their name above for more details. Minimum night requirements apply depending on the season.
- RATES: Starting at $125 a night based on double occupancy with at least a 2 night minimum.
- WALK: There are several restaurants within walking distance, and the quaint downtown of Vero Beach is a little over 2 miles north.
- PETS: Pets are not allowed.
4150 NE Indian River Dr.
Jensen Beach, FL 34957
Old-Florida charm with updated interiors located just across the street from the Intracoastal Waterway, the Driftwood Motel and Cottages has been family owned and operated since 1958. Offering suites, one bedroom apartments and stand-alone cottages, all with full eat in kitchens. The Honeymoon Cottage (pictured above) has an additional cozy front sitting room. A two night minimum stay is required during holidays and local special events.
- RATES: Cottages start at $109 during the off season; click their name above for rate details.
- WALK: Conchy Joe’s Seafood Restaurant is a short walk south, and downtown Jensen Beach with many great shops and restaurants is just under a mile away.
- PETS: Pets are welcome with some restrictions, call for details.
WEST PALM BEACH
1410 Georgia Ave.
West Palm Beach, FL 33401
Experience South Florida hospitality at this family owned boutique style luxury Inn and cottages. Casa Grandview offers Inn guestrooms and suites, self-catering vacation cottages and an Art Deco building with self-catering suites available for weekly or monthly occupancy, all within a compound of gorgeous shade and palm trees, tropical flowers, intimate walkways and two swimming pools. Amenities abound; too many to list here but “wet bar” “Tesla charging stations” “spa robes” and “TiVo” caught our attention. Click on their name above for gorgeous photos and to choose your cottage – some are circa 1911!
- RATES: Art Deco building suites start at $149, Inn rooms start at $199 (and come with an amazing gourmet 3-course breakfast), vacation cottages start at $179.
- WALK: Casa Grand View is located in the Flamingo Park Historic District which is mostly residential and there are a few restaurants within walking distance. The very vibrant downtown is 1.5 miles away.
- PETS: Some accommodations are dog friendly, check the website.
THE FLORIDA KEYS
99360 Overseas Highway
Key Largo, FL 33037
Tropical grounds with its own private beach facing the sunset, Sunset Cove offers cottages, waterfront suites, connecting rooms, standard motel rooms and some “fun and interesting accomodations” (RV’s, including a vintage Airstream, some with full kitchens and some with kitchenettes.) All of the stand-alone cottages have full kitchens or full kitchen efficiancys. Click their name above for more details and to choose your cottage. All accommodations are equipped with A/C, cable TV and microwave. Some amenities are tiki huts, beach lounges, complimentary coffee, pastries and juice, registered guests have free use of kayaks and paddleboards. Dock, ramp and trailer parking are available for a fee.
- RATES: The smallest cottage – The Hideaway, with a bar fridge and microwave – is $160. The other stand-alone cottages are $225.
- WALK: A number of good restaurants are within walking distance, including top-rated Mrs. Mac’s Kitchen, and Bayside Grill and Sunset Bar for live music overlooking the water.
- PETS: Pets are welcome at some of Sunset Cove’s accommodations; check their site for details.
84959 Overseas Highway
Islamorada, FL 33036
Whether Drop Anchor’s palm tree shaded grounds and gardens beckon you to relax under tiki huts overlooking the water, or a swim in the waterfront pool is more your thing, peace and tranquiltiy abounds. Drop Anchor’s cottages do share a wall, making them not technically free-standing, but our experience in our jewel box of a cottage – yes, it felt exactly like our own place, we heard no noise, we felt complete privacy – was one of the most idyllic, lovely stays ever for the Triple B Team. Our Room 14B Cottage is attached to the large Room 14 Cottage which is a airy tropical-themed cottage with 2 bedrooms, full kitchen and living and dining are, perfect for families or girls’ getaways. There are other cottages available, as well as suites (some oceanfront) and a tropical oceanfront trailer. Some units have kitchenettes, some full kitchens; click on their name above to choose your perfect accommodation.
- RATES: At the time of our stay the Room 14B Cottage was $190. Check rates by clicking their name above.
- WALK: There are two restaurants within easy walking distance: Hog Heaven Sports Bar and Grill (which is nicer than the name may imply, and has gorgeous water views) and Island Grill (also with water views.)
- PETS: Pets are not allowed.
LITTLE CONCH KEY
62250 Overseas Highway
Little Conch Key, FL 33050
Truly a Florida best-kep-secret, Conch Key Cottages are off the beaten path and so private – on their own Key! – you’ll never want to leave. Three beach front honeymoon-style cottages are made from Dade County pine and have vaulted beamed ceilings and screened porches. Other accommodations range from 1/1 Island Rooms and 1/1 Island Apartments (these are in a 4-plex) to a 1/1 Baby Conch Cottage, a 2/2 Family Garden Cottage, to 2 luxury estate homes offering 5 bedrooms and 5.5 bathrooms each (a 7 night minimum is required for the luxury estate homes.) There are more accommodations offered, click on their name above for full details. Amenities are many, including continental breakfast, Wi-Fi throughout the entire resort, fully equipped kitchens, heated and cooled swimming pool, lending library, personal BBQ, 2 person sea kayak, and more, click the link for the full list.
- RATES: Rates are seasonal, click the link to visit their reservations page. A sampling: in August an Island Room is $154, the Baby Conch Cottage is $249.
- WALK: Little Conch Key is “an island, entire of itself” (to misquote John Donne; sorry, John) with no need to walk anywhere, but for an evening out there are several restaurants at Duck Key – just 1.5 miles south – including Angler and Ale at the Hawks Cay Resort.
- PETS: Pets are allowed at the luxury estate homes, click the link for details.
Key West is another cottage- and bungalow-filled town deserving of its own article – coming soon!
Every single time we settle into a bungalow style hotel we say to each other, “This is all we need. This! Is ALL we need! This is all we NEED.” How about you? Let us know where you’ve stayed- in your ‘own’ place – and not wanted to leave so we can add it to our list!