An Alluring Slice of Island Life
If variety is the spice of life, then La Siesta’s bold selection of upscale suites, colorful cottages, and contemporary-cool villas packs a punch. Tulum-inspired on the outside, our signature oceanfront cottages offer modern amenities inside, including space to entertain and a patio for beachside bonding. Seeking your own piece of paradise? Our well-appointed villas are the perfect carefree escape for groups and families, with everything from full kitchens to private yards and patios. Be swept away by the beauty of Islamorada with each bespoke stay.
In-Room Amenities
Ocean Front Cottage
Beachfront Casitas
Our oceanfront, standalone cottages feature an open floor plan with king bed and a sleeper sofa. Step right onto the beach from your cottage and watch the water lap at the shore from your own private patio space.
Oceanfront One Bedroom Accessible Cottage
Beachfront Casitas
These one-bedroom oceanfront, standalone cottages feature a king bed with an open living and dining space for up to four guests. Enjoy a picturesque patio area right on the beach, roll-in shower, and other accessible amenities.
Casa de Juan
Coastal Villas
This secluded, contemporary two-bedroom vacation rental offers an open floor plan with high ceilings. The living and dining area features a full kitchen for entertaining a full kitchen. Gather with friends and family on the private patio deck surrounded by a tropical garden. This is the ideal retreat to enjoy the island serenity of Islamorada.
Dos Palmas
Coastal Villas
This bi-level suite offers two bedrooms. Located on the second floor is the master bedroom with a luxurious king bed while the second bedroom offers two queen beds. Enjoy space for up to eight guests with two full bathrooms, a spacious living and dining area, and a beautiful ocean views from your private patio.
Casa de Coco
Coastal Villas
Live your Florida Keys dream in the palm-shaded Casa de Coco House. This ranch style, three-bedroom home features one bedroom with a king bed, one bedroom with a queen bed, and one bedroom with double queen beds. Enjoy a full kitchen to gather together and private covered patio.
Sea Glass House
Coastal Villas
Our beach-style, three-bedroom Sea Glass House features two stories and a lovely garden view that transforms morning coffee and lunch breaks into a true escape. Its secluded location and private patio make it the perfect retreat to embrace the laid-back Florida Keys lifestyle.
Islamorada Resort Collection
200th Anniversary Sale - Islamorada Resort Collection
Celebrate The Florida Keys’ 200th anniversary and the island’s place in Florida’s history.
Islamorada Resort Collection
Florida & Georgia Resident Special - Islamorada Resort Collection
Kick back and relax on a tropical beach vacation. We offer Florida and Georgia residents up to 20% off our best available rate.
La Siesta Resort & Villas
Home Sweet Islamorada
Don't miss these exclusive savings on our unique villas in Islamorada.
Pelican Cove Resort & Marina | Postcard Inn Beach Resort & Marina | La Siesta Resort & Villas
Splash & Play in the Ocean
Enjoy the Ultimate Thrill Ride. Our incredible island jetski tour takes you through over 26 miles of the most beautiful waters and scenery the Florida Keys has to offer.
Amara Cay Resort | La Siesta Resort & Villas
Sun, Snorkel & Sandbar
Treat yourself to a trip to the Keys with a $150 credit to use toward snorkel and sandbar tours.
La Siesta Resort & Villas
Love is Brewing
A tasting experience at Islamorada Brewing & Distilling, local chocolates, and $100 resort credit create the perfect recipe for romance.
Islamorada Resort Collection
Sea More This Summer - Islamorada Resort Collection
Looking to get more out of your summer? Look no further! We're gifting you a free night so you can "sea" more during your summer vacation.
Islamorada Resort Collection
Vacation From Inflation - Islamorada Resort Collection
It's the return of our Vacation from Inflation sale. Instead of raising prices, we're offering up to 40% off your summer vacation.
More Places to Stay
Amara Cay Resort
Vacation at your own pace at Amara Cay Resort. Our boutique spaces bring a vibe of luxe leisure while staying true to the effortless simplicity the Keys are famous for. Discover captivating views of the Alligator Reef Lighthouse, and boating excursions and amenities that let you embrace authentic island life.
Pelican Cove Resort & Marina
Escape to a peaceful Florida Keys resort on the sunrise side of Islamorada. Enjoy your own private beach lagoon at Pelican Cove Resort with Wild & Lime poolside bar, a swimming pool, jet ski tours, and an on-site marina. This tranquil paradise provides guests with as much, or as little, activity as you desire.
Postcard Inn Beach Resort & Marina
Wake up to the sun rising over the ocean at Postcard Inn Beach Resort & Marina for a day filled with watersports and endless fun. This lively resort is home to 14 acres of beach, legendary waterfront dining options, two pools, resort activities, a full-service marina, and an on-site dive center.