# Island Bay Resort Beachfront Cottages In The Florida Keys *By James Hills — Updated March 2025* When planning a romantic getaway, few things top the idea of a beachfront room ... except for a private cottage right on the beach. That's what Island Bay Resort offers and instead of those mega-resorts that you might find on South Beach, these cottages are laidback and relaxed. There's no long hallways to walk down or extra fees to worry about. Instead, you just park your car right next to the room and start relaxing the moment you open the door. ***NOTE: at the time of writing (1/12/2020) Island Bay Resort is currently listed as being for sale. Before discovering this though, the owner (who hosted us for this stay) expressed to us that he and his wife love the property and hope to stay here for a long time into the future. As such, details contained in this review / feature may change in the future. *** ### What To Expect on Your First Viking River Cruise Here's what to expect on your first Viking River cruise through Europe including a personal experience exploring Christmas Markets along the Rhine. ManTripping [Read More](https://ads.flowmediamarketing.com/go/oWyfSwhyUMFI2YpPea5Huw.418) ### Date Night Cookbook and Activities for Couples: Recipes and Games for a Romantic Night In A date night cookbook with recipes and games for couples who want a romantic evening in together. Amazon (affiliate) [Check Price on Amazon](https://ads.flowmediamarketing.com/go/oWyfSwhyUMFI2YpPea5Huw.2078) ### We're Not Really Strangers Couples Edition Card Game for Date Nights A 150-card conversation game for two, made for memorable date nights and game nights, ages 15 and up. Amazon (affiliate) [Check Price on Amazon](https://ads.flowmediamarketing.com/go/oWyfSwhyUMFI2YpPea5Huw.2074) Promoted by FlowAds Island Bay Resort is located on Tavernier Key, about halfway between [Key Largo](https://fla-keys.com/key-largo/) and [Islamorada](https://fla-keys.com/islamorada/). This makes it an almost perfect location for a weekend escape from Miami as well as a halfway point on your journey to Key West. It also provides a quiet relaxed spot that makes it easy to explore all of the cool stuff in the upper Florida Keys.  The property is a long narrow piece of land located right off the Overseas Highway, extending right to the water. Island Bay Resort includes 10 cottages, three Tiki Huts, beach chairs, a dock, watersports equipment (paddleboards and kayaks), laundry facilities, as well as charcoal grills by every room. In short, it has literally everything you'd need for a perfect romantic getaway and the landscaping, as well as maintenance, is meticulous. In fact, that's where I met the owner as he was out one morning raking the sand to ensure it was clean and looked good visually. ## Man Gear Pick of the Month September's Pick Amazon (affiliate) ### Kenyon City Grill Portable Stainless Steel Electric Grill Why we picked it: a grill you can actually carry to the campsite, the tailgate or the cabin without borrowing a truck. Stainless, no propane tank to wrestle, and hot enough to cook for four guys rather than reheat for one. [Check The Price](https://ads.flowmediamarketing.com/go/y2FtkA16CrhxDKtWBBu6iQ.2144) [August's Pick LiberNovo Maxis Electric Big and Tall Ergonomic Office Chair, Graphite 52cm $1,393.00](https://ads.flowmediamarketing.com/go/y2FtkA16CrhxDKtWBBu6iQ.2350) [July's Pick Powerful Propane Torch Gun, Adjustable Flame Thrower Gun, Kitchen Torch with Detachable Design, Flamethrower Blow Torch for BBQ, Searing Steak, Welding, Camping Charcoal Lighter(Tank Not Included) $42.99](https://ads.flowmediamarketing.com/go/y2FtkA16CrhxDKtWBBu6iQ.2397) [June's Pick OYASUMI Funny BBQ Man Hot Dog Holders, 4 PCS Reusable Stainless Steel Sausage Stands, Portable Hot Dog Roasters, Barbecue Grill Accessories for Camping & Party Gifts $7.98](https://ads.flowmediamarketing.com/go/y2FtkA16CrhxDKtWBBu6iQ.2396) Promoted by FlowAds Each of the 10 cottages features a slightly different theme and ours, Key West cottage #1 featured a very cool and kitschy Key West, Florida theme. Other cottages pay homage to other Keys and aspects of the Florida Keys, including Boats and Birds #2, Flora and Fauna #3. Occupancy is limited to two people per cottage so the max number of guests you'll ever find here is 20. Just that element alone makes it that much more special ... almost like your own personal escape. While our room was very comfortable and the internet connection was very good as well, the reason why you are staying here is ultimately the opportunity to relax and enjoy the view as well as maybe play in the water a bit too.  Luckily, the property was perfect for this to the point where I wish I had been able to stay a couple more days to just relax and enjoy the beach instead of running around to various places we were supposed to cover. However, we did enjoy the sunset with a bottle of wine served up in Tervis tumblers since it is Florida. Honestly, in a world where luxury has become commonplace and everyone seems to be competing on amenities and features, there seem to be fewer and fewer places like Island Bay Resort. While I enjoy fancy luxury resorts, there's one luxury that you really can't replicate authentically. That's the sense of being connected to nature and in particular the ocean. Ironically, I feel like those resorts that do add fancy amenities designed to bring you closer ... in fact ultimately put barriers up between you and that feature they are trying to highlight. [Island Bay Resort](https://www.islandbayresort.com/) does things with the perfect balance though. They've nailed it with the things that are important - comfortable clean room with a good bathroom, sheets, and mattress. Then they've developed the property to serve your enjoyment and not distract from it. Whether it's kayaking around the calm waters or sitting in a chair with a glass of wine while someone special sits beside you - this is the place to do it. Island Bay Resort is special and has that personal touch that most other properties lack. This comes from not just the attention to detail with maintaining the property but even showcasing the owner's photos on a digital picture frame in the room and the individual theme and decor of the rooms. This is a special place and Island Bay Resort is the perfect place for a Florida Keys romantic weekend getaway. September's Pick Kadún Hotel Boutique ### Kadún Hotel Boutique Why we picked it: a boutique hotel in the middle of Cabo San Lucas rather than a compound outside it - you walk to Medano Beach and the marina instead of waiting on a shuttle, which is the whole difference on a long weekend. [Book with Flow Voyages](https://ads.flowmediamarketing.com/go/PWQSz3FatqsMCNZWPa_4dQ.2145) [Marriott Cancun, An All-Inclusive Resort](https://ads.flowmediamarketing.com/go/PWQSz3FatqsMCNZWPa_4dQ.2146) [Margaritaville Island Reserve Riviera Maya](https://ads.flowmediamarketing.com/go/PWQSz3FatqsMCNZWPa_4dQ.2147) [Casa Velas](https://ads.flowmediamarketing.com/go/PWQSz3FatqsMCNZWPa_4dQ.2148) Promoted by FlowAds Details Written by: James Hills Published: 12 January 2020 Last Updated: 01 March 2025 ### 🚢Ready To Book A Vacation? Let us help you plan a cruise, all-inclusive resort, or tour for your next guys trip, family vacation, or romantic getaway. Click here to [**Book Your Next Vacation**](https://www.mantripping.com/vacation-planning.html). #### Which Style Of Amazon Cruise Should You Pick To Explore World's Largest River? Aug 17, 2026 [Which Style Of Amazon Cruise Should You Pick To Explore World's Largest River?](https://www.mantripping.com/travel/amazon-river-cruise-planning-ship-options.html) [Plan Your Next Vacation Today!](https://www.mantripping.com/vacation-planning.html) ### Products & Gift Ideas #### Nocs Zero Tube Monocular Review - The 7.2 Ounce Optic That Packs Easily and For EDC Oct 04, 2026 [Nocs Zero Tube Monocular Review - The 7.2 Ounce Optic That Packs Easily and For EDC](https://www.mantripping.com/stuff/nocs-zero-tube-monocular-review.html) #### LiberNovo Maxis Chair Review - Finally A Seat That Lets Big Dudes Feel Comfortable At The Desk Sep 10, 2026 [LiberNovo Maxis Chair Review - Finally A Seat That Lets Big Dudes Feel Comfortable At The Desk](https://www.mantripping.com/stuff/libernovo-maxis-big-and-tall-office-chair-review.html) #### FRESKO 4-in-1 Immersion Hand Blender Review Sep 09, 2026 [FRESKO 4-in-1 Immersion Hand Blender Review](https://www.mantripping.com/stuff/fresko-4-in-1-immersion-hand-blender-review.html) ### Top Guys Trip Ideas: #### Norwegian Encore Is The World's Best Ship For A Guys Getaway Dec 18, 2019 [Norwegian Encore Is The World's Best Ship For A Guys Getaway](https://www.mantripping.com/travel/norwegian-encore-is-the-best-ship-ever-for-a-guys-getaway.html) #### Active Vacation Ideas for Every Type of Man Dec 05, 2018 [Active Vacation Ideas for Every Type of Man](https://www.mantripping.com/travel/active-man-vacation-ideas.html) #### Why Men Should Pick A Dominican Republic All-Inclusive Resort For A Caribbean Guys Trip Jul 26, 2023 [Why Men Should Pick A Dominican Republic All-Inclusive Resort For A Caribbean Guys Trip](https://www.mantripping.com/travel/men-should-pick-dominican-republic-all-inclusive-resort-for-next-caribbean-guys-trip.html) ### Related Articles #### The Best Places to Go Prospecting and Treasure Hunting in America [The Best Places to Go Prospecting and Treasure Hunting in America](https://www.mantripping.com/travel/best-places-to-go-prospecting.html) #### Hemlock Neversink Adult Summer Camp in the Catskills Just Added a 53-Foot Climbing Tower [Hemlock Neversink Adult Summer Camp in the Catskills Just Added a 53-Foot Climbing Tower](https://www.mantripping.com/travel/hemlock-catskills-adult-summer-camp.html) #### Rockets, Fishing Charters And Surf On A Florida Space Coast Guys Trip [Rockets, Fishing Charters And Surf On A Florida Space Coast Guys Trip](https://www.mantripping.com/travel/florida-space-coast-guys-trip.html) #### Psychics, Sacred Vortexes, & Nine Places That Even Skeptics Will Enjoy Visiting on a Guys Trip [Psychics, Sacred Vortexes, & Nine Places That Even Skeptics Will Enjoy Visiting on a Guys Trip](https://www.mantripping.com/travel/metaphysical-guys-trip-destinations.html) #### Orlando Golf Trip? Here's Why Florida's Cannabis Laws Will Catch You Off Guard [Orlando Golf Trip? Here's Why Florida's Cannabis Laws Will Catch You Off Guard](https://www.mantripping.com/travel/florida-cannabis-laws-visitors-snowbirds-orlando.html) - [**](https://www.mantripping.com/search.html) - [**](https://www.mantripping.com/sitemap.html) - [** Polls](https://www.mantripping.com/polls.html) - [Community Login](https://www.mantripping.com/registration/login.html) - [Brand Engagement Newsletter](https://www.mantripping.com/pr-ops-newsletter.html) - [Links](https://www.mantripping.com/links.html) - [Pitch Portal](https://www.mantripping.com/pitch.html) - [Men's Travel Survey](https://www.mantripping.com/the-mantripping-guys-trip-report-spring-2026.html) --- *Source: [Island Bay Resort Beachfront Cottages In The Florida Keys](https://www.mantripping.com/romantic-getaways/island-bay-resort-beachfront-cottages-in-the-florida-keys.html)* **Tags:** Florida Guys Trip Ideas, Romantic Getaway, Beach Resorts, Romantic Resort