Last Updated on May 8, 2024 by Marybeth
Because Siesta Key is brimming with a plenitude of vintage vacation rentals and the cutest cottagey motels (as well as oceanfront condos and luxurious mansions if that’s your thing) everyone’s vacation-in-the-sun wishes can be met. With just two bridges leading to this barrier island – and the popularity of this beach town (thank you, Dr. Beach and all you others choosing Siesta Key Beach as your #1 pick) especially in season, the need for large scale anything isn’t, well, needed.
And don’t you spend most of your time outside the room while on holiday by the beach?
Certainly we all want the spot where we’ll be laying our sun-tired heads at the end of the day to be comfortable and clean. And hopefully curated with a mix of creativity and modern amenities. (For us that means a cozy couch big enough to sprawl with a couple of glasses of wine and a remote control. If there’s cool local art on the walls, that’s great too.)
Just a stroll down any street leading to Siesta Key Village and you’ll be enchanted by playful, affordable, and retro-stylish vintage properties: stand-alone homes, small 2-story renovated condos built in the 60s, and clusters of cottages surrounded by palm trees and often set around a gorgeous swimming pool. Our mission is to share with you the best non-chain places to stay and to dine all around Florida, and today, in Siesta Key. Places where families, moms and pops, and small business owners often man the front desk, manage their own social media, and take pride in their town.
Let’s visit the charming small-density accommodations available for you to experience. We may not have found ALL of them (let us know in the comments) but we have gathered many great resources for you to get started:
COTTAGE HOTEL PROPERTIES WITHIN WALKING DISTANCE TO SIESTA KEY VILLAGE & THE BEACH
Because while on vacation some of us tend to relax our healthy eating standards, walking gives us that go-ahead to indulge. SO many restaurants beckon to us from Siesta Key Village, the choices are endless (we’ll show you some at the end of the article and link to their sites.)
Built in the 1940s, all three cottages are 2/1 and have been meticulously updated with central A/C and heat, fully equipped kitchens, pull-out sofa or daybed in the living room, king size bed in one bedroom and a full size bed in the 2nd (in the Blue Dolphin the 2nd bedroom has a twin size.) Click on their site name above for more details about these adorable, authentic old-Florida cottages located just 300 ft. to the beach!
The Beach Palms Suite is a 1/1 with a spacious living room with a pull out sofa, a king bedroom, and a full kitchen, and private outdoor gas grill.
Less than 150 steps from the beach and a 3 minute walk to the village, BeachPoint Cottages offers studio-size rooms with 1 bed and 1 bath to free-standing cottages – 2/1 and 2/2. Your pre-approved dog is welcome in certain cottages; click on the property name above for details about bringing your fur baby, more photos of each cottage, and the list of amenities. Use their rate calculator to find your exact price for your proposed dates and cottage choice.
Every unit at the Sandbox is beachfront! Family owned since 1998, this old-Florida vacation spot offers a studio unit (queen Murphy bed) ; 2 1-bedroom units with a king size bed and a pull-out queen sleeper; a 2/2 with a king, queen, and a pull-out queen; and a 3/2 with two king rooms and a 2-twins. All rooms have been newly remodeled with tiled kitchens, baths, and new furnishings. All 1, 2, and 3 bedroom units have fully equipped kitchens. The studio unit has a kitchenette. Dogs are welcome! See their rental policies for details. Visit their site by clicking on the name above.
Colorful cottages surround a heated swimming pool at this quiet property where you can lounge in the shade of the palms or the tiki hut. Or walk for approximately 3 minutes to the beach! Rooms and suite choices begin with a studio queen or king with a kitchenette, to 1- or 2-bedroom suites with full self-catering kitchens. The “Owner’s Suite” 2/2 is an option that can be enlarged using adjoining suites for a 4/4 accommodating up to 14 people. Click their name above for exact pricing for your dates and room choices.
Built in 1928 by John Ringling as housing for his seasonal employees, this property is certainly more vintage than most on our list. Completely updated and recently refreshed, this amazing piece of history is just .1 miles to Public Beach Access #10 and a half mile to the Village. Choose from an Economy Apartment, Standard, Superior, or Deluxe; all with full kitchens and can sleep from 4 to 6 people. A large heated swimming pool, outdoor grills, beach umbrellas, towels and chairs are some of the amenities. Pets are accepted for an additional charge. Click their name for current pricing.
Boutique-style hotel accommodations can be found at Tropical Breeze Resort (not to be confused with Tropical Breeze Resorts further south on the island.) Multiple room choices range from studio-sized with a kitchenette; studio suite with a full kitchen; studio suite with a king and bunk beds; 1, 2, or 3 bedrooms with queen sleeper sofas; or the Honeymoon Suite, their most luxurious suite for your special occasion. Two resort swimming pools with tropical landscaping are on site, as well as numerous shaded private seating areas throughout the resort. Take a look at their site for accurate pricing and room styles. The beach is a short walk away and the Village is just around the corner.
VACATION RENTAL AGENCIES WITH PROPERTIES WITHIN WALKING DISTANCE OF SIESTA KEY VILLAGE & THE BEACH
On the Flipside Cottage
147 Avenida Veneccia •. 941-757-8226
AMI – Anna Maria Island – Locals rental agency has a greater concentration of available properties in Anna Maria, understandably, but also offer several rental homes in Siesta Key and Lido Key. The Flipside cottage is a delightfully vintage 1940s 2/1 recently refreshed. Enjoy the outdoor patio and grill and indoor foosball table. The beach access is just 400 ft. away and the Village is less than 5 minutes on foot.
335 Canal Rd. • 941-322-4086
Siesta Beach Rentals has several of these colorful condo buildings (built in the 60s perhaps? I couldn’t find out) that fill us with nostalgia – “the elixir of memory + love” (I borrowed that from Coastal Living.) Choose from 1/1 or 2/2; all units have access to large swimming pools, hammocks, BBQs, tiki bar. Fully equipped kitchens and laundry in unit. Pet friendly. The 335 Canal Rd. building is a 2-minute walk to Morton’s Siesta Market and all that the Village has to offer!
303 Canal Rd. • 941-349-5500
Another colorful throwback condo building just across the street from Morton’s Siesta Market (but buffered from the commercial area by a large lush row of trees.) This 2/2 sleeps 6 with 1 king, 2 twins, and a sofa sleeper. 303 shares a pool with one other unit. The condo has a washer/dryer. Small dog allowed with pet fee. Rates start at $270 and this unit has a 1-week minimum. Siesta 4-Rent offers numerous rentals – with up to 7 bedrooms – around Siesta Key; visit their site, above, to peruse them all.
This 4/3, built in the 1940s, with a heated swimming pool is larger than it looks from the outside and sleeps up to 11 people. Tall palm trees offer shade in this quiet, mostly residential area close to the Village. You can bring your small dog for an additional fee. The listing says 1 block to the beach but make note, once you reach the Public Beach Access #8 the extremely wide Siesta Key Beach will have you walking another “block” or 2. One week minimum rental starts at $2200/week and $7500/month.
VACATION RENTAL COTTAGES LISTED WITH AIRBNB OR VRBO WITHIN WALKING DISTANCE TO SIESTA KEY VILLAGE & THE BEACH
Heated Pool, 4 Houses to the Beach
Located just next door to the Art Deco house above, this home is divided into two rentals; each are a 1/1 and you can either rent the upstairs unit or the first floor. (Or both for the extended fam!) The master bedroom has a king bed and the pull-out sleeper is a queen. The two units share a heated swimming pool. We read somewhere that this cute home was once part of the Ringling Beach Hotel compound, built in 1954, which makes it even more intriguing! Check the AirBnb listing, click above, for current pricing; the listing quotes $262/night for the 2nd floor unit, and alternatively lists a maximum of 3, and also 4, people are allowed. (We’re guessing the correct number must be 4, considering the bed types/sizes.)
145 Beach Rd.
Tiny but mightily cute, this studio + kitchenette is perfect for a couple. Set back from the road, beside/behind a larger vintage cottage, (available at Postcard Vacation Rentals, see above) The Love Shack is right across the street from Public Beach Access #4. Siesta Key Village is just a block away but this part of Beach Rd. is residential and quiet. Pre-approved dogs are welcome for an additional $50 non-refundable fee. Rates are approximately $150/night, check the site for current pricing.
424 Canal Rd.
This lovely 3/2 sleeps 6 and was built in 1955. Beautifully updated, with a full kitchen, Manatee Cottage boasts an outdoor shower and a laundry facility shared with the Dolphin Cottage (a 1/1 also available on VRBO.) You’ll be just a 5 minute walk to Public Beach Access #7, and the owner has provided a beach wagon to easily your bring your chairs, toys, etc. Siesta Key Village is two blocks away from this quiet, shady home. 1 pre-approved pet is allowed. Approximate rates start at $361, check the site for current pricing.
348 Canal Rd.
Built by the Archibald family, who were partially responsible for the planned community of Siesta Key, this 1948 gem has been carefully updated yet retains its original Pecky Cypress cedar walls and ceilings as well as the hardwood floors throughout. Larger than some other homes on our list at 1500 sq. ft., Rad’s Cozy Cottage offers 2 bedrooms – one king bedroom and a 2-twin bedroom, with a pull-out sofa bed and can accommodate 6 people. Private backyard with a heated pool, outdoor shower and grill, and a private dock (bring your kayaks! Or rent some) located just across the street are some of the amenities, along with a cooler, beach toys, wagon and beach chairs. Rates start at approximately $550, visit the site for your dates and current pricing.
WITHIN DRIVING/BIKING DISTANCE TO SIESTA KEY VILLAGE & CLOSE TO TURTLE BEACH
Turtle Beach is the lesser-known, not as wide or powdery white as the famous Siesta Key Beach but its lack of notoriety makes it appealing for less crowded sunsets and less of a walk from the parking lot. Turtle Beach is located about 5 miles south of the Village.
8212 Midnight Pass Rd.
Siesta Key Bungalows is an old-Florida cottage style motel set on Heron Lagoon (perfect for exploring by kayak) on a shaded property with a swimming pool. At the date of publication the lodging’s website states it is closed for renovations by the new owners, Gertrude Rentals. A search of Gertrude’s site has reservations available, and we’ve linked to their waterfront Ringling Bungalow, above, because we stayed there some years ago and that was where the idea for our blog was born!
Related: Where it all Began: the Birth of This Florida Travel Blog
Siesta Key Bungalows is tucked away off of Midnight Pass Rd. and about a mile to Turtle Beach. Wide bike lanes allow for a safe, approximately 6 minute bike ride to the beach. There are several types of rooms available – some are waterfront, most are not – at various prices; check Gertrude’s site for current pricing.
9049 Midnight Pass Rd. • 941-349-4554
The Turtle Beach Resort is pet- and kid-friendly! The Turtle Beach Inn is the more romantic part of the property, reserved for adults only. The Resort features 2/1 cottages sleeping 4-6 people, 1/1 cottages for 2 people, and two townhouses – a 2/2 and a 2/3 – that sleep up to 6 people, and all have their own private hot tubs. Some are waterfront, others are water view. The Inn cottages are all 1/1 or studios with 1 bath, and all have private, intimate patio hot tubs. Swimming pool, complimentary use of bikes, fishing gear, kayaks and canoes are just some of the amenities. Rates start at approximately $240 for mid-September, visit their site for accurate seasonal pricing for your room choice. The Turtle Beach Resort & Inn is less than half a mile to Turtle Beach.
A drive down Midnight Pass Road will take you past so many condo rental resorts your head will spin – most of them with a typical condo look that will make your eyelids droop. We did find three that are delightfully vintage and a couple that have that 1960s continuous w-shaped roofline that I’ve been trying to find the name of and finally did – FOLDED PLATE ROOFLINE, designed by architect Donald Wexler in the 60s.
Check out Siesta Sun Beach Villas, Seacrest on Siesta Key, and Siesta Royale.
If we’ve missed any let us know! Even we can’t find them all, though you could say I’m a tiny bit fixated on finding ALL the vintage vacation options!
And around the Village, some of the best restaurants and shops you’ll want to visit:
