Vacation Rentals By Owner In Islamorada, FL

We have recently completed an inside and outside renovation. The Bayview Villa is a private, secluded villa facing Florida Bay and in view of the fabulous Everglades and gorgeous sunsets. Quick access to offshore fishing. Located in a lush tropical hammock in a quiet, one acre residential area (rare). The villa is approx. 30 feet from the water. The property contains a wading beach and a free marina with night lights, power and water. An enclosed patio offers private outdoor grill and dining.brbrThe villa itself comes with a fully-equipped new stainless kitchen, full size LG washer and dryer, linens, two queen and one king beds, Cable TV, and a dining room. French doors in the dining area face the bay, spacious 700 square foot patio,and marina giving the feeling of the outdoors being in. Beautiful glass block showers with pebble floors are in both baths. brbrIslamorada proudly calls itself the 'Fishing Capital of the World' but there is so much more to do

Bayview Villa- Pet-Friendly Waterfront Paradise. A fisherman's dream!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$207.85

Step into your own slice of paradise at this sunlit, open-concept home overlooking the turquoise waters of the Florida Keys. With enchanting views from nearly every room, Tollgate Tides is the perfect retreat for a surf trip with friends, a romantic couples' getaway, or a family vacation by the shore.brbr⭐ Location Highlightsbr • Robbie's of Islamorada (10 miles): Feed the famous tarpon, book a fishing charter, or browse local artisan shops.br • Long Key State Park (10 miles): A must for kayaking, snorkeling, and beach picnics.br • Windley Key Fossil Reef Geological State Park: Walk through ancient coral trails and enjoy prime birding.br • Local seafood dining: Savor the catch of the day at waterfront restaurants or take a sunset cruise for unforgettable views.brbr Why You'll Love Itbr • Outdoor living: Spacious waterfront patio for grilling your fresh catch, alfresco dining, or simply soaking in the coastal breeze.br • Gourmet kitchen: Fully equipped with stainless steel appliances, a wine fridge, and bar/island seating perfect for gathering.br • Relaxation: End your day with a soak in the jetted tub or stream your favorite movies with HBO and Netflix.br • Activities for all: Sneak in a tennis match on the shared courts, explore nearby state parks, or enjoy family time with games in the living area.br • Everyday comforts: Private washer/dryer, central AC, and wide-clearance access for ease of mobility.brbr Amenities at a Glancebr • High-speed internet + streaming (HBO & Netflix)br • Oceanfront views from balcony, deck & patiobr • Shared tennis courtsbr • Jetted tub for ultimate relaxationbr • Fully equipped kitchen with wine fridgebr • Private washer/dryer & central ACbr • Snowbird-friendly for extended staysbrbr✨ Tollgate Tides blends comfort and adventure in one perfect waterfront escape. Whether you're here for fishing, snorkeling, sunset cruises, or simply soaking up the tropical vibe, you'll find everything you need to make unforgettable Florida Keys memories.brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.

Radiant waterfront retreat with remarkable views, patio, tennis court, & grill

Islamorada, Florida, United States

Bed

Bath

Sleeps

$246.11

Beacon Reef 404 - Beautiful two-bedroom two baths, condo with everything that you need for a perfect relaxing vacation. Balcony access off your living room and master bedroom that overlooks the newly remodeled pool and jacuzzi as well as the beach and ocean. The complex is oceanfront and has amazing views of the Atlantic. Some additional amenities: chairs and tables on balcony, printer, tiki hut by pool, and undercover parking. brIf booking more than a year in advance current prices may not reflect the annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Condo

Charming 2BR condo in Islamorada with pool, hot tub, and beautiful views.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$353.01

This home is the definition of 'Keys' living. Situated on an oversized lot this 3 bedroom, 3 bath home offers 68 feet of dockage including a 10,000 lb. boat lift, a spacious wraparound porch overlooking the canal, outdoor entertainment area including a large tiki hut with TV. The main living area offers 2 bedrooms, 2 bathrooms, a well-maintained kitchen, and an open concept living area perfect for entertaining. With vaulted ceilings, multiple sliding glass doors, and expansive gable windows, this home feels light, bright, and airy. As a bonus, the downstairs offers a private studio apartment with a bathroom and private entry. Placed in one of the most desirable boating locations, you are minutes away from some of the best fishing spots in the world. brEnjoying the natural beauty of the florida keys. Watch the sunrise from Anne's beach, enjoy an abundance of wildlife right in the canal with visiting manatees, parrotfish and pelicans. Only 5 Min By Boat To Atlantic Ocean And 15 Min To The World Famous Alligator Reef For Some Of The Best Snorkeling The Florida Keys Have To Offer. Located in one of Lower Matecumbe's favorite neighborhoods, Tollgate Shores is only minutes away from downtown Islamorada, Founders Park and Marathon. brbrAnne's Beach - ‪6 min walk‬brRobbie’s of Islamorada - ‪6 min drive‬brFiesta Key - ‪7 min drive‬brBud n' Mary's Dive Center - ‪10 min drive‬

NEW! Waterfront, 3 Bedroom, 3 Bath. Keys Living, Peaceful Retreat

Islamorada, Florida, United States

Bed

Bath

Sleeps

$540.79

Welcome to your Islamorada escape in the highly sought-after Port Antigua community. This canal-front pool home is set up perfectly for families and groups who want space, dockage, and that true Keys outdoor lifestyle.brbrUpstairs features 2 bedrooms and 2 bathrooms with a comfortable, open living space designed for relaxing after a day on the water.brbrDownstairs offers a separate 2 bedroom, 1 bath suite with a kitchenette — ideal for extended family, friends, or multi-generation stays while still giving everyone their own space.brbrStep outside and you'll find what makes this home special:br• Heated pool for year-round enjoymentbr• Outdoor kitchen perfect for grilling the day's catchbr• 65 feet of dockagebr• Quick boating access to the Ocean or Baybr• Access to the private Port Antigua homeowners beachbrbrBring your boat, enjoy the sunsets, and settle into the laid-back Keys lifestyle. This is the kind of home guests come back to year after year.brIf booking more than a year in advance current prices may not reflect annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Spacious 4BR canal home in Islamorada with private heated pool and beach access.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$307.57

141 Ocean Lane - The Beach Fixes Everything. That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in Lower Matecumbe Key, the two-bedroom, two-bathroom house offers a 270-degree view of the Atlantic. Check out that view as you lounge in the living area, take an afternoon snack in the kitchen or when you rise from bed in either the master bedroom or the upstairs guestroom. Better yet, you can enjoy the surroundings while you grill out on the screened porch that wraps around nearly the entire home. brThe main upstairs living space contains a master king bedroom with attached bath and a queen guestroom. The tiled kitchen and living room offer ample cooking space, another flat screen TV and two-sided views of the sea. For an added bonus this home comes with kayaks and bikes for your everyday adventure!! brThere's plenty of outdoor action beyond the porch as well. Lounge on the outdoor dock (30') and tie off your boat for almost instant access to Islamorada's famed oceanside fishing grounds. When your day on the water is done, prep your catch at the home's private fish cleaning station. brbrNear the house is the small Anne's Beach. There are nature trails, boardwalks to small lunch and BBQ areas, private sandy areas hidden in the mangroves and parking. The home is also near Robbie's Marina (where they feed the Tarpon), Bud n' Mary's Marina and Caloosa Cove Marina. You won't have a problem finding a marina for boat rentals or a fishing guide (Deep Sea or Backcountry). You are only minutes away from Downtown Islamorada where Worldwide Sportsman and the Islamorada Fish Company are located yet you are in a quiet area of town.brbrYou will be able to truly enjoy your vacation! This is a great house that our tenants seem to love and will want to return to year after year! Located at Mile Marker 76, this home is available for monthly rentals. brbrIf booking more than a year in advance current prices may not reflect the annual cost of living increase. Many of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Relax in this 3-bedroom canal home with stunning views in Islamorada!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$232.76

This Modern Upscale duplex Home Has All The Amenities For A Wonderful And Special Vacation. King Size Master Bedroom And Queen Size Second Bedroom,sofa Bed In Living Room,extra folding bed, 4 Balconies, Gas BBQ, Satellite TV and WiFi. Carport For Two Cars. Pool, Tiki Hut. End Unit Provides Extra Sunlight And More Privacy. Boat slip .Boat rental available Washer Dryer in unit. Storage shed.Bike path at our door.Security front gate

Islamorada Paradise! Luxury Townhouse! Sleeps 4-6 Boat Slip And Pool

Islamorada, Florida, United States

Bed

Bath

6

Sleeps

$246.32

Welcome to your stunning 2 bed/2 bath “Keys Vibe” condo in the heart of Islamorada—also known worldwide as the Sport‑Fishing Capital of the World . Immerse yourself in barefoot‑luxury with: 28 day minimum rental required. brbrProperty Highlightsbr • Spacious living: Two comfortable bedrooms and two full baths—perfect for families or friends.br • Resort-style amenities: Dive into the pool, energize in the gym, melt stress away in the sauna, or unwind at the club house.br • Private pier: Ideal for sunrise coffee, evening cocktails, or casting a line.br • Truly Keys ambiance: Salt‑sprayed air, swaying palms, relaxed lifestyles.brbr Prime Islamorada LocationbrbrYour retreat sits centrally in Islamorada—just minutes from top attractions and activities.brbr⸻brbrThings to Do NearbybrbrDrawn from trusted Florida Keys and Islamorada guides.brbr Fishing & Boatingbr • Charter epic sport‑fishing trips—Islamorada’s world‑class fishing scene is unmatched .br • Explore reefs by boat, snorkel shipwrecks, or relax on local sandbars, including the popular Islamorada SandBar .brbr Marine Encountersbr • Theater of the Sea: Swim with dolphins, sea lions, sharks—or just enjoy animal shows and boat rides .br • Visit Robbie’s Marina to hand-feed tarpon—an unforgettable, Instagram‑ready highlight .brbr State Parks & Naturebr • Wander through Windley Key Fossil Reef Geological State Park to see fossilized coral and explore nature trails .br • Kayak or hike around Indian Key and Lignumvitae Key State Parks, stepping into rich history and lush native foliage .br • Chill at Anne’s Beach, with calm shallow waters, lovely boardwalks, picnic spots, and even kiteboarding .brbr Culture & Museumsbr • Explore the History of Diving Museum, featuring vintage helmets, old‑school diving gadgets, and ocean lore .br • Learn your way through Florida Keys history at the Florida Keys History & Discovery Center and more local museums .brbr Art & Shoppingbr • Stroll through the Morada Way Arts District, especially lively during the monthly Art Walk .br • Discover handmade art and souvenirs at Rain Barrel Village, with its iconic giant lobster sculpture “Betsy” .brbrLocal Flavors & Treatsbr • Sample fresh seafood, lively bars, local craft beer and innovative burritos at Village Square stops like Bad Boy Burrito .br • Don’t miss key‑lime pie at the Blond Giraffe Key Lime Pie Factory .brbr⸻brbrRelax & Unwind Ideasbr • Enjoy serene afternoons at your condo pool, sauna, or pier—escape the world and soak in the Keys lifestyle.br • Sip cocktails at your clubhouse with new friends, or toast the sunset as pelicans glide overhead.br • Jump on your bike or rent e‑bikes to cruise along the Keys Overseas Heritage Trail .brbr⸻brbrStay with Us for:br • Easy access to fishing charters, snorkeling, diving, and sandbar adventures.br • Cultural richness—from art galleries and museums to friendly bars and local breweries.br • Resort‑style comforts and prime location for exploring Islamorada’s vibrant spirit.

Condo

Paradise in the Heart of Islamorada.Come relax and have the time of your life!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$172.63

Rates are based on 28 day rental with check in and check out on Saturday. Contact owner for flexible check in dates.brbrCome relax in paradise in the heart of the Florida of Keys. Relax by the heated pool overlooking the turquoise bay; fish from the dock, snorkel in the protected cove. Enjoy the clear, turquoise waters, breathtaking views and beautiful sunsets from the roof top viewing deck.brbrOur newly remodeled studio offers all the amenities of home: a fully-equipped kitchen including microwave, oven, refrigerator, ice-maker and dishwasher. Fresh, clean bathroom with all linens provided. The bathroom has just been completely remodeled. The unit is immaculately clean. No smoking and no pets.brbrThis unit can comfortably sleep up to 2 adults. There is a queen size murphy bed and a full size futon and both are very comfortable.brbrbrThe large, tropical bay front condo complex is beautifully landscaped and offers a variety of activities: a large, heated swimming pool, sauna, exercise room, activities and game room (Friday nights are poker night), adult billiard room, barbecue facilities, park area, and more.brbrSnorkel, lobster, sail, fish, and swim in our protected cove. Relax on the rooftop terrace for the best sunset around! For your convenience there is lighted parking, coded security gate, secured building and laundry facilities.brbrLocated in the Heart of Islamorada, you will have easy access to Islamorada Founders Park which has a sandy beach, boat ramp, sports facilities, skate park, and more. Additionally world-class fishing and diving, excellent restaurants/night life and plenty of 'fun in the sun' activities are just minutes away.

Apartment

Lovely Islamorada Studio in the Heart of the Keys

Islamorada, Florida, United States

Bed

Bath

Sleeps

$253.13

Our home is in Islamorada, in the middle Florida Keys. To be more specific, we are on Lower Matecumbe Key, which is the southernmost island in Islamorada, at exactly Mile Marker 74, on the bayside. Our home is a 2/2, and can comfortably sleep four, with two bedrooms upstairs. The Master has a queen bed, and a private bath. The second bedroom has twin beds, and a separate bath. If more room is needed, or for families with young kids or teenagers, it's possible for at least two to camp out on comfortable air mattresses upstairs in the family room. Downstairs there is a laundry room/workshop, and a more rustic game room/bar with a refrigerator for water/soft drinks/beer/bait.

Beautiful 2/2 Islamorada Home Directly on Florida Bay (28 Day Minimum Rental)

Islamorada, Florida, United States

Bed

Bath

Sleeps

$752.66

Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island setting. Unwind at the zero-entry pool, Tiki Bar, or private beach with hammocks. Guests enjoy kayaking, snorkeling, access to restaurants and services across sister resorts, plus convenient access to snorkeling and local culture.brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 300 sq. ft, equipped with complimentary toiletries, standard quality 37-inch TV, available with Standard cable, and Premium cable.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool available all year, opened from 8:00AM to 5:30PM.brAdditional features:br • Heated poolbrbr✦ Free parking lot – 1 space(s).brbr✦ Shuttle service is available upon reservation between 7:00AM and 11:00AM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 nonrefundable fee per pet per day/ max 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Refundable security deposit charged nightly. brbr✦ Complimentary shuttle within 4 miles. brbr✦ Early check-in & late check-out subject to availability for a fee.br br✦ Smoking prohibited indoors; designated smoking areas provided.

2 Rooms w/ Balcony, Courtyard View, Outdoor Pool, Free Parking & Pet Friendly

Islamorada, Florida, United States

Bed

Bath

8

Sleeps

$541.07

Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island setting. Unwind at the zero-entry pool, Tiki Bar, or private beach with hammocks. Guests enjoy kayaking, snorkeling, access to restaurants and services across sister resorts, plus convenient access to snorkeling and local culture.brbrThis listing is for a room within a hotel.brbr✦ Your room is 264 sq. ft, equipped with complimentary toiletries, standard quality 37-inch TV, available with Standard cable, and Premium cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool available all year, opened from 8:00AM to 5:30PM.brAdditional features:br • Heated poolbrbr✦ Free parking lot – 1 space(s).brbr✦ Shuttle service is available upon reservation between 7:00AM and 11:00AM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 nonrefundable fee per pet per day/ max 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Refundable security deposit charged nightly. brbr✦ Complimentary shuttle within 4 miles. brbr✦ Early check-in & late check-out subject to availability for a fee.br br✦ Smoking prohibited indoors; designated smoking areas provided.

Courtyard View King Room w/ Balcony, Outdoor Pool & Free Parking

Islamorada, Florida, United States

Bed

Bath

3

Sleeps

$807.75

Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy heated pools, Sidecar poolside bar, water sport rentals, marina access, and shared benefits across three resort properties—including shuttles, dining, and leisure facilities.brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 540 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool available all year.brAdditional features:br • Heated poolbrbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $55.13 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 per pet per day, with a max of 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The front desk is open daily from 7 AM to 11 PM with your information and keys ready. After hours, you’ll be directed to a nearby sister resort for check-in.brbr✦ The required refundable security deposit is charged per night on a valid credit card.

2 Suites w/Queen Beds, Kitchenette, Outdoor Pool, Free Parking & Pet Friendly

Islamorada, Florida, United States

Bed

Bath

12

Sleeps

$851.56

Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy heated pools, Sidecar poolside bar, water sport rentals, marina access, and shared benefits across three resort properties—including shuttles, dining, and leisure facilities.brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 450 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool available all year.brAdditional features:br • Heated poolbrbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $55.13 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 per pet per day, with a max of 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The front desk is open daily from 7 AM to 11 PM with your information and keys ready. After hours, you’ll be directed to a nearby sister resort for check-in.brbr✦ The required refundable security deposit is charged per night on a valid credit card.

One Bedroom Suite w/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly

Islamorada, Florida, United States

Bed

Bath

12

Sleeps

$946.09

Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy heated pools, Sidecar poolside bar, water sport rentals, marina access, and shared benefits across three resort properties—including shuttles, dining, and leisure facilities.brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 1350 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool available all year.brAdditional features:br • Heated poolbrbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $55.13 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 per pet per day, with a max of 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The front desk is open daily from 7 AM to 11 PM with your information and keys ready. After hours, you’ll be directed to a nearby sister resort for check-in.brbr✦ The required refundable security deposit is charged per night on a valid credit card.

2 Separate Unites w/ 2 Bedrooms, Kitchenette, Pool, Free Parking & Pool

Islamorada, Florida, United States

Bed

Bath

16

Sleeps

$1018.15

Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront suites with premium amenities. Guests enjoy heated pools, Sidecar poolside bar, water sport rentals, marina access, and shared benefits across three resort properties—including shuttles, dining, and leisure facilities.brbrThis listing is for a room within a hotel.brbr✦ Your room is 850 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool available all year.brAdditional features:br • Heated poolbrbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $55.13 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 per pet per day, with a max of 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The front desk is open daily from 7 AM to 11 PM with your information and keys ready. After hours, you’ll be directed to a nearby sister resort for check-in.brbr✦ The required refundable security deposit is charged per night on a valid credit card.

Two Bedrooms Suite w/Ocean View, Pool, Free Parking & Pet Friendly

Islamorada, Florida, United States

Bed

Bath

8

Sleeps

$389.29

Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island setting. Unwind at the zero-entry pool, Tiki Bar, or private beach with hammocks. Guests enjoy kayaking, snorkeling, access to restaurants and services across sister resorts, plus convenient access to snorkeling and local culture.brbrThis listing is for a room within a hotel.brbr✦ Your room is 300 sq. ft, equipped with complimentary toiletries, standard quality 37-inch TV, available with Standard cable, and Premium cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool available all year, opened from 8:00AM to 5:30PM.brAdditional features:br • Heated poolbrbr✦ Free parking lot – 1 space(s).brbr✦ Shuttle service is available upon reservation between 7:00AM and 11:00AM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 nonrefundable fee per pet per day/ max 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Refundable security deposit charged nightly. brbr✦ Complimentary shuttle within 4 miles. brbr✦ Early check-in & late check-out subject to availability for a fee.br br✦ Smoking prohibited indoors; designated smoking areas provided.

2 Queen Beds Room w/Patio, Outdoor Pool, Free Parking & Pet Friendly

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1231.82

Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront suites with premium amenities. Guests enjoy heated pools, Sidecar poolside bar, water sport rentals, marina access, and shared benefits across three resort properties—including shuttles, dining, and leisure facilities.brbrThis listing is for a room within a hotel.brbr✦ Your room is 850 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool available all year.brAdditional features:br • Heated poolbrbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $55.13 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 per pet per day, with a max of 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The front desk is open daily from 7 AM to 11 PM with your information and keys ready. After hours, you’ll be directed to a nearby sister resort for check-in.brbr✦ The required refundable security deposit is charged per night on a valid credit card.

Two Bedroom Ocean Front Suite w/Kitchenette, Pool, Free Parking & Pet Friendly

Islamorada, Florida, United States

Bed

Bath

6

Sleeps

$580.46

Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island setting. Unwind at the zero-entry pool, Tiki Bar, or private beach with hammocks. Guests enjoy kayaking, snorkeling, access to restaurants and services across sister resorts, plus convenient access to snorkeling and local culture.brbrThis listing is for a room within a hotel.brbr✦ Your room is 264 sq. ft, equipped with complimentary toiletries, standard quality 37-inch TV, available with Standard cable, and Premium cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool available all year, opened from 8:00AM to 5:30PM.brAdditional features:br • Heated poolbrbr✦ Free parking lot – 1 space(s).brbr✦ Shuttle service is available upon reservation between 7:00AM and 11:00AM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 nonrefundable fee per pet per day/ max 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Refundable security deposit charged nightly. brbr✦ Complimentary shuttle within 4 miles. brbr✦ Early check-in & late check-out subject to availability for a fee.br br✦ Smoking prohibited indoors; designated smoking areas provided.

Courtyard View Room w/Patio, Outdoor Pool, Free Parking & Pet Friendly

Islamorada, Florida, United States

Bed

Bath