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- 12 Best STR Finds | April 29, 2025
12 Best STR Finds | April 29, 2025
The Market's Top Short Term Rentals – Yours Before Anyone Else.
May 10, 2025 | Issue # 170 |
STR DAILY
Hey, friend! Today’s properties include a cabin in Boulder with a 28% cash-on-cash return, a cottage in Naples with $13K in free cash flow, and a mid-century masterpiece in Palm Springs with more than $208K in projected bookings.
Could one of these be your next income-producing gem? Let’s make this the year you get the property that changes your life. Enjoy and good luck!

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TODAY’S TOP PROPERTIES

Here’s what I love about it – Naples’ cutest cottage (NO HOA!) flaunts vaulted ceilings and TWO screened lanais that lap up SWFL sunshine—lanai lounging? Mandatory. 2022 upgrades deliver ceramic-tiled flair indoors and a pergola-shaded backyard primed for al fresco lounging. Projected bookings of $44.2K yield $13.7K in cash flow and a 13.5% cash-on-cash return—proof that paradise can pay its own way. A single-car garage, ample driveway, and Bayshore breezes a stroll away mean beach-bound ROI has never been breezier.
Price: $399,000
BR/Bath: 2 Bedroom / 1 Bath
Sq. Feet: 988
Avg. Daily Rate: $216
Expected Occupancy Rate: 56%
Expected Annual Revenue: $44,194
Expected Annual Cash Flow: $13,732
Expected Cash on Cash: 13.51%

Here’s what I love about it – Two lots from the sand, this Kitty Hawk beachside stunner ditches four tight bedrooms for three spa-worthy suites—room to breathe, room to bank. Bright open-concept living swaps stove duty for salt-kissed breezes and seaside dining detours. A lower-level studio with private entry (and laundry) doubles as a mini-rental hideaway or VIP guest pad. Cornhole-ready backyard and storm-tested hurricane shutters mean fun’s on-call from sunrise beach runs to tempest nights. With projected bookings north of $61K, this coastal retreat brings in the tide—and the returns.
Price: $575,000
BR/Bath: 3 Bedroom / 3 Bath
Sq. Feet: 1,580
Avg. Daily Rate: $299
Expected Occupancy Rate: 56%
Expected Annual Revenue: $61,462
Expected Annual Cash Flow: $17,853
Expected Cash on Cash: 12.06%

Here’s what I love about it – Mid-century modern masterpiece meets Palm Springs panache on a sprawling 17,860 sq ft canvas, complete with a private pool and resort-style yard. Open-concept living flows into a detached, solar-powered guesthouse—perfect for solo travelers, co-owners, or Insta-glampers craving desert chic. Approved plans for a garage and carport? Blueprint-ready expansion in a STR-permissible zone. With projected revenue topping $208K, $76K in cash flow, and an 18% cash-on-cash return, this turnkey estate is as smart as it is stylish. Poolside glamour with sunburning ROI—no sunscreen required.
Price: $1,695,000
BR/Bath: 5 Bedroom / 5 Bath
Sq. Feet: 2,678
Avg. Daily Rate: $974
Expected Occupancy Rate: 59%
Expected Annual Revenue: $208,222
Expected Annual Cash Flow: $76,154
Expected Cash on Cash: 18.28%

Here’s what I love about it – Vaulted ceilings, a wood-burning stove, and a hummingbird soundtrack on 1.63 acres just minutes from Downtown Boulder—where mountain air meets Starlink speeds. Sunlit living flows effortlessly into a walkout basement with Jack-and-Jill baths (plus a handy half bath off the great room for guests). Certified septic, an oversized garage, and mostly paved roads mean modern comfort with alpine charm. Projected $63.7K cash flow and a 28.8% cash-on-cash return? Peak ROI, no altitude adjustment needed. Open house 5/3, 10 – 1: come for the views, stay for the yield.
Price: $890,000
BR/Bath: 3 Bedroom / 3 Bath
Sq. Feet: 1,624
Avg. Daily Rate: $632
Expected Occupancy Rate: 59%
Expected Annual Revenue: $136,541
Expected Annual Cash Flow: $63,658
Expected Cash on Cash: 28.81%

Here’s what I love about it – Sun-drenched freedom formula—no HOA, no rental rules, just pure SWFL bliss in Poinciana Village. Four bedrooms, two baths, and a heated pool sanctuary meet a game room prepped for ping-pong playoffs and luxury vinyl floors that shrug off wear and tear. A stainless-steel kitchen arsenal and storage-packed laundry room make hosting feel effortless, while white-sand beaches and Downtown Naples are just a 10-minute cruise. With $24.9K in annual cash flow and a 13% cash-on-cash return, this turnkey retreat proves in Naples, the tides raise all boats. Pool floats optional, profit tides guaranteed.
Price: $749,000
BR/Bath: 4 Bedroom / 2 Bath
Sq. Feet: 1,840
Avg. Daily Rate: $334
Expected Occupancy Rate: 67%
Expected Annual Revenue: $81,954
Expected Annual Cash Flow: $24,902
Expected Cash on Cash: 13.06%

Here’s what I love about it – Resort-round-the-clock Poconos living—this turnkey 2-bed, 1-bath retreat comes fully furnished with modern furniture, kitchenware, and a hot tub tucked under its enclosed gazebo; just pack your suitcase. Minutes from pools, lakes, tennis courts, Route 80, Mt. Airy Casino, Kalahari Resort, and Camelback slopes, this hotspot is a vacationer’s playground. HOA and township approvals mean STR income starts day one. With projected bookings of $33.7K, $12.6K in cash flow, and a 17% cash-on-cash return, your capital gets the VIP treatment. This property’s ROI is hotter than its hot tub.
Price: $269,900
BR/Bath: 2 Bedroom / 1 Bath
Sq. Feet: 1,040
Avg. Daily Rate: $200
Expected Occupancy Rate: 46%
Expected Annual Revenue: $33,683
Expected Annual Cash Flow: $12,585
Expected Cash on Cash: 17.36%

Here’s what I love about it – Lakefront charm and Bluegrass flair collide at this 936 sq ft, 2-bed/1-bath cabin on Elmer Davis Lake—fully furnished, guest-approved, and just an hour from Kentucky’s bourbon trails and Cincinnati lights. Sip sunrise coffee where water frontage begs for a private dock, or detour 30 minutes to Buffalo Trace’s mint-julep magic (Ark Encounter excursions are the cherry on top). With 71% occupancy fueling $43.5K in bookings and $20K+ annual cash flow (28.7% cash-on-cash), this retreat pours profit like a top-shelf whiskey. Lakefront living? Check. Bourbon-side returns? On tap.
Price: $275,000
BR/Bath: 2 Bedroom / 1 Bath
Sq. Feet: 936
Avg. Daily Rate: $169
Expected Occupancy Rate: 71%
Expected Annual Revenue: $43,542
Expected Annual Cash Flow: $20,846
Expected Cash on Cash: 28.71%

Here’s what I love about it – Lakefront lovability: this 2-bed, 1-bath charmer sits a quarter mile from Calhoun boat ramp—launch party ready with seasonal water vistas across the road. Fully furnished and turn-key, it nets $30K in bookings, over $12K cash flow, and a 20% cash-on-cash splash. Inside, stylish updates pair with cozy nooks, perfect for lazy dock days or hosting wave-rider crowds. Fishing lines, kayak launches, or simply lakeside lounging—the choice is yours. ROI? As refreshing as a dawn cast off the dock.
Price: $225,000
BR/Bath: 2 Bedroom / 1 Bath
Sq. Feet: 912
Avg. Daily Rate: $155
Expected Occupancy Rate: 53%
Expected Annual Revenue: $30,026
Expected Annual Cash Flow: $12,185
Expected Cash on Cash: 20.02%

Here’s what I love about it – Touchdown territory—this remodeled two-story corner lot gem sits just a mile from Notre Dame’s Golden Dome, draped in hardwood floors and anchored by a masonry wood-burning fireplace built for pregame huddles. Custom built-ins flank the hearth (perfect for fight song vinyl or bookworm trophies), while the coffee bar–kitchen combo fuels early morning study sessions. The finished lower level moonlights as an extra bedroom or victory lounge, and the deck beckons for tailgate-worthy gatherings. With $19.8K in projected cash flow and a 13.9% cash-on-cash return, it’s a winning play for both hosts and investors. Game day? You’re already in the end zone.
Price: $499,900
BR/Bath: 5 Bedroom / 3 Bath
Sq. Feet: 2,761
Avg. Daily Rate: $436
Expected Occupancy Rate: 37%
Expected Annual Revenue: $58,305
Expected Annual Cash Flow: $19,758
Expected Cash on Cash: 13.86%

Here’s what I love about it - A real-life fairy tale cottage nestled on 7 private acres, brimming with custom built-ins, hardwood floors, whimsical stained glass, and a sunken wood-stove nook begging for storybook evenings. Follow garden paths beside a babbling brook through enchanted woods to your own Moon Lake frontage—next-level serenity included. A whole-home generator keeps the magic lit when sprites slip away, and a detached workshop with bonus guest room is poised for your finishing touches. Currently enchanting Airbnb guests, this 2BR/2BA gem conjures $47K in bookings, $19.5K in cash flow, and a 20.6% cash-on-cash return. Proof that happily ever after can also mean happily ever profit—no wand required.
Price: $349,900
BR/Bath: 2 Bedroom / 2 Bath
Sq. Feet: 1,400
Avg. Daily Rate: $211
Expected Occupancy Rate: 61%
Expected Annual Revenue: $47,311
Expected Annual Cash Flow: $19,485
Expected Cash on Cash: 20.62%

Here’s what I love about it – Park-like paradise meets hand-hewn log nostalgia at Laurel Landing, a 2-bed, 1-bath Maggie Valley gem where blooming laurels and a rocking-chair porch set the stage. Fully furnished—down to the dishes—this 10+-year STR champion boasts a stone-clad fireplace, hot tub soak sessions, and chink-style warmth straight out of a storybook. Winter mornings get extra cozy with a new energy-efficient insert, while the hot tub whispers “relax.” With projected bookings of $33.2K (10.5% gross yield), rustic vibes and solid returns share the same porch swing. Start the adventure—and your ROI—before the steam settles.
Price: $315,000
BR/Bath: 2 Bedroom / 1 Bath
Sq. Feet: 840
Avg. Daily Rate: $168
Expected Occupancy Rate: 54%
Expected Annual Revenue: $33,215
Expected Annual Cash Flow: $9,384
Expected Cash on Cash: 11.61%

Here's what I love about it - Sun-soaked Coral Shores stunner, fully revamped in 2021 with impact windows, new roof, plumbing, and electrical—modern peace of mind meets coastal chic. Just minutes from Las Olas Boulevard and Fort Lauderdale’s glittering beaches, this 3-bed/2-bath retreat is equally at home as a dreamy long-term residence or turnkey Airbnb. Fully furnished and primed for guests, it’s where high-end finishes and palm-tree panoramas collide. Projected bookings hit $86.2K with $28.5K in annual cash flow and a 15.3% cash-on-cash return—returns as bright as the Florida sun. Beachside buzz meets bottom-line beauty—catch this wave before it sails away.
Price: $749,999
BR/Bath: 3 Bedroom / 2 Bath
Sq. Feet: 1,359
Avg. Daily Rate: $362
Expected Occupancy Rate: 65%
Expected Annual Revenue: $86,223
Expected Annual Cash Flow: $28,554
Expected Cash on Cash: 15.34%
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Buying a short term rental doesn’t need to be complicated. But, with more than 14,000 listings hitting the market every single day, the likelihood of you finding the right home at the right time feels damn near impossible.
You need to find the right location.
With the right unit economics.
And, the right style.
It’s tough.
But, when you do… it’s a game life changer.
The last Airbnb I purchased provides a 16.99% Cash on Cash return with $15,700+ in annual free cash flow after my mortgage and all expenses…
I hope this is a resource that saves you time, so you can make decisions in minutes and avoid missing out on the property that will change your life.
Disclaimer: The information provided on STR Daily is for informational purposes only and should not be considered financial advice. Short-term rental regulations change constantly, so please review local rules and regulations prior to any purchases. Projected cash-on-cash returns are based on a 20% down payment, estimated furnishing costs appropriate for the property size, and anticipated fees. Actual returns may vary. Please run the numbers yourself or consult a financial professional to assess risks and develop a strategy suited to your specific needs.