Experience Tranquility in a Charming Cottage Rental in Key West, FL

Escape to our charming Tranquility Cottage Rental in Key West, FL and indulge in a peaceful vacation for 2. Experience the perfect mix of comfort and convenience, with top amenities and nearby activities for a memorable stay.

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Rates & Availability  
(Displayed in USD)

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• Rates From $350 to $1,128 per night

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Featured Amenities

Property Features

Entertainment

Other Property Amenities

Health Beauty Spa, Marinas, Boat Rentals & Excursions, Museums, Key West Aquarium, Hangers, Kitchen, Antiquing, Paddle Boarding, Dolphin Watching, Wildlife Viewing, Fishing - Surf, Hiking, Banana Boat Riding & Water Tubing, Wind Surfing, Ocean Waterpark & Challenge Course, Kayaking, Kite Boarding, Pickleball, Tennis, Golfing, Banks, Grocery Stores, Scuba Diving, Public Parks & Beaches, Key West Historic Seaport, Key West Tropical Forest & Tropical Garden, Skydiving, Southernmost Point Buoy, Dry Tortugas National Park & Fort Jefferson, Fort Zachary Taylor State Park & Beach, Sunset Celebration at Mallory Square, History Tours - Motorized, Walking & Biking, The Florida Reef - N. America’s only living coral barrier reef, Key West Marine Park stretching from Higgs Beach to South Beach , The Key West Butterfly & Nature Conservatory, Dining Out, Live Theater, Concerts & Entertainment, Food Tours, Ghost Tours, Pub Crawls, Your reservation guest portal will provide details, Your reservation guest portal will provide details, Your reservation guest portal will provide details, Paint & Sip Art Classes, Cable, Coffee Maker - Drip, Cleaning: Optional, Dishes & Silverware, Fire Extinguisher, Hot Water, Smoke Detector, Bird Watching, Boating, Eco Tourism, Shopping, Fitness Centers, Hospital, Laundromats, Cycling, DeepSea Fishing, Fishing - Backcountry , Jet Skiing, Para-sailing, Fishing - Pier, Racquetball, Sailing, Snorkeling, Swimming, Cooking Basics, Not Necessary, Living Room, Historic District, Street Parking, Deck Patio Uncovered, Historic, Romantic, Tourist Attractions, Fenced Yard, Dining table

Testimonials

June 1, 2022 - Website
Ann Street is Amazing! by Jill K.
Celebrated our 20th anniversary, found this gem! Beautiful, cozy unit that is close to all the action, but not noisy! Private pool is very cool. Clean and well maintained grounds (and unit) Excellent service and would recommend 110%. We did all the museums and rented bikes for the week (no parking so it was perfect) Kept bikes on porch and explored the island!Manager's ResponseThank you for your Five Star review of Ann Street Tranquility. We are so glad that you enjoyed the beautiful, cozy cottage, the pool and the location. We hope to welcome you back soon!
Thank you for your Five Star review of Ann Street Tranquility. We are so glad that you enjoyed the beautiful, cozy cottage, the pool and the location. We hope to welcome you back soon!

April 1, 2022 - Website
Cozy Cottage by Recent Guest
We spent nine nights in the cottage and our experience was wonderful. Nice set up and great location. Quiet retreat in an otherwise busy Old Town location. Manager's ResponseThanks for your feedback about Ann Street Tranquility. Your review perfectly describes this nicely appointed, tranquil cottage hidden so close to bustling Duval Street. We hope you visit again soon!
Thanks for your feedback about Ann Street Tranquility. Your review perfectly describes this nicely appointed, tranquil cottage hidden so close to bustling Duval Street. We hope you visit again soon!

March 1, 2022 - Website
Awesome by Recent Guest
Stayed here for a week. Cottage is clean and comfortable. Private deck is a great way to unwind with a cocktail after a day at the beach or a day of exploring the island. Loved the pool. Felt like it was our private pool since we didn’t see anyone all week. Highly recommend this cottage!! Manager's ResponseThank you for your Five Star Review of Ann Street Tranquility. We are so glad you enjoyed the cottage, deck and pool. We greatly appreciate your recommendation and look forward to welcoming you back soon!
Thank you for your Five Star Review of Ann Street Tranquility. We are so glad you enjoyed the cottage, deck and pool. We greatly appreciate your recommendation and look forward to welcoming you back soon!

January 1, 2022 - Website
Charming and Comfortable by Recent Guest
Enjoyed the cottage and patio. Clean, comfortable, and charming. All he amenities one could want.

November 1, 2021 - Website
We love it by Michael T.
We just love staying at Ann St tranquility. as always dealing with Rent Key West has been great. despite a plumbing problem that was resolved they comped us the night anyway. And when we chose to extend our stay they charged us the rate we agreed upon when I first booked months ago. They are an honest company to deal with and we always feel welcome there. It feels like home. To call up every year to book, they know us and are so easy to work with. I cant say enough good things about them. Thank you .

October 1, 2021 - Website
Resort level service at a Rental by Recent Guest
We were blown away by the service provided by Rent Key West Vacations. From our booking date on, Dean was available to address any of our concerns. We had a very early flight into Key West and they accommodated us by storing our luggage at their rental office. We were prepared to return to pick them up but they had them delivered to our rental. Beyond Amazing! We will definitely rent with Rent Key West Vacations Again.

October 1, 2021 - Website
Great spot steps from Duval but doesn't seem that way! by Sean H.
My wife and I spent a week at Ann Street Tranquility. We could not be more pleased with the cottage. It is in a great location just walking distance from all the popular spots of Old Town. That said, it was also plenty quiet and we could relax by the pool and sleep well even though we know there was serious partying happening just a hundred yards away. Cottage is perfect for two and we will definitely plan to return here in the future! Also, we think it would be a great spot to go with a group but everyone can have their own cottage (5 in the location).

September 1, 2021 - Website
Ann Street Cottage by Recent Guest
The property was immaculate...the furniture very uncomfortable. Pillows on chairs, bed and even the throw pillows really need to be replaced. The sofa springs must in need of repair. Wicker chairs very uncomfortable. Instructions for remote for television need to be supplied. There were 2 remotes there, one marked Samsung like the tv. Using it all we got was streaming channels. Property manager came and showed us the correct remote for viewing live tv. Pool was nice. Parking expensive. It was quiet as promised. It was convenient to Duval St. Would have liked information about activities. Overall we enjoyed our stay in Key West just wish we had visited about 50 years ago. It is not geared at all to senior citizens or non-drinkers!

July 1, 2021 - Website
Great location! by Craig J.
We had a great stay at the Tranquility. It was perfect for two.

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