Vacation Rentals By Owner In Islamorada, FL

$660.31

3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed!

Islamorada, Florida, United States

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ facilities.brbrThis listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.brbr✦ Each room is 301 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 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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $150 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

3

Bed

3

Bath

12

Sleeps

$483.81

/ Nightly

Apartment

Get Ready for Blissful Getaway! 2 Relaxing Units, Onsite Pool, Free Breakfast

Islamorada, Florida, United States

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ 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 290 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 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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.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 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

2

Bed

2

Bath

8

Sleeps

$483.81

/ Nightly

Apartment

Vacation At its Finest! 2 Convenient Units, Free Parking, Breakfast, Onsite Pool

Islamorada, Florida, United States

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ 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 290 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 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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.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 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

Bed

Bath

Sleeps

$434.25

/ Nightly

Apartment

Escape The Hustle and Bustle! 2 Classy Units, Free Parking, Onsite Pool

Islamorada, Florida, United States

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ 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 301 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 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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.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 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

2

Bed

2

Bath

8

Sleeps

$434.25

/ Nightly

Apartment

Pets are Allowed Here! 2 Comfortable Units, Free Breakfast, Parking, Pool

Islamorada, Florida, United States

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ 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 301 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 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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.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 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

2

Bed

2

Bath

8

Sleeps

$974.21

/ Nightly

Apartment

Snorkeling & Kayaking Beach Resort! Seaside Villa w/Patio! Marina, Parking

Islamorada, Florida, United States

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ facilities.brbrThis listing is for 4 separate rooms within a hotel. The price shown in the listing covers all 4 rooms.brbr✦ Each room is 290 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 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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.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 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

Bed

Bath

Sleeps

$660.31

/ Nightly

Apartment

Dive Into Your Dream Vacation! 3 Spacious Units, Onsite Pool, FREE Breakfast!

Islamorada, Florida, United States

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ facilities.brbrThis listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.brbr✦ Each room is 301 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 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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $150 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

Bed

Bath

Sleeps

$660.31

/ Nightly

Hotel

Everything You Need For The Perfect Vacation! 3 Convenient Units, FREE Parking!

Islamorada, Florida, United States

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ facilities.brbrThis listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.brbr✦ Each room is 301 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 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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $150 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

3

Bed

3

Bath

12

Sleeps

$483.81

/ Nightly

Apartment

Better Choice for your Vacation! 2 Pet-Friendly Units, Free Breakfast, Pool

Islamorada, Florida, United States

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ 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 290 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 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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.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 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

Bed

Bath

Sleeps

$434.25

/ Nightly

Apartment

Make Your Trip More Enjoyable! 2 Convenient Units, Pets Allowed, Onsite Pool

Islamorada, Florida, United States

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ 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 301 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 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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.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 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

Bed

Bath

Sleeps

$2145.49

/ Nightly

Private Vacation Home

Discover 'The Oasis': a stunning 3-bedroom retreat in Islamorada with a heated private pool.

Islamorada, Florida, United States

Set on nearly three private acres with 200 feet of secluded Atlantic shoreline, The Oasis is a truly rare Islamorada estate offering space, privacy, and one of the most unique features in the Florida Keys — a heated saltwater pool positioned directly on the ocean itself.brbrThis exclusive compound consists of two separate homes, thoughtfully designed for comfort and flexibility. The main residence offers one bedroom and 1.5 baths, while the guest house features two bedrooms and one bath. Each home includes its own kitchen and living area, allowing families or groups to gather together while still enjoying private space when desired.brbrThe grounds are expansive and beautifully maintained, framed by towering palms and open water views in every direction. Spend your days launching one of the four kayaks or two paddleboards from your private beach, cruising the neighborhood on one of six bicycles, or enjoying a game of bocce ball or cornhole as the ocean breeze rolls in.brbrModern comforts are seamlessly integrated throughout, including enterprise-grade high-speed Wi-Fi, a Tesla charging station, professional mosquito control service, five 50” smart TVs, and stainless steel appliances.brbrPet friendly and ideally located in the heart of Upper Matecumbe — just 0.7 miles from Publix and minutes from Islamorada's best dining, marinas, and sandbars — The Oasis delivers something exceptionally hard to find in the Keys: acreage, beachfront, an oceanfront pool, and total privacy, all in the center of town.brbrIf 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. brVACATION RENTAL LICENSE: 24-0120 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.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.

Bed

Bath

Sleeps

$650.15

/ Nightly

Private Vacation Home

Island pool home awaits in Islamorada's Port Antigua

Islamorada, Florida, United States

Your island pool home awaits in Islamorada's Port Antigua! 3,500 square foot, 4 bedroom, 3 bathroom, high ceilings, tile & hardwood floors, state of the art kitchen w/ concrete counters & top of the line stainless appliances. Open, spacious and perfect for entertaining is how this home was designed. Walk out the great room french doors into an intimate pool setting with custom chickee & lounge area decorated with a vibe of Gilligan's Island meets The Ritz Carlton. Out back is 65ft of yacht dockage w/ shore power & water for water toys. Rare 2 car garage with golf cart, fishing rods, ping pong table/ game room, and bicycles provided. Private beach 1 minute by golf cart & ramp for owners in this golf cart approved community on Lower Matecumbe in Islamorada, the Village of Islands.

Bed

Bath

Sleeps

$748.56

/ Nightly

Private Vacation Home

Oceanfront Islamorada Townhome- Private Dock, Pool & Pet-Friendly

Islamorada, Florida, United States

Welcome to your oceanfront Florida Keys vacation rental in the heart of Islamorada!brThis luxury 3-bedroom, 3-bath townhouse at Peaceful Palms offers the perfect blend of comfort, style, and location for your next tropical escape. From peaceful sunrises over the Atlantic to private dock access and a resort-style oceanfront pool, everything is here to help you relax and recharge.brbrStep into a bright, open living space with coastal-inspired décor, a fully stocked kitchen, and private balconies with ocean views. With three full bathrooms (two en suite), this family-friendly retreat is ideal for couples, small groups, or even those working remotely in paradise.brbrWhat You'll Love:brOcean views from the master suite and private balconybrbrPrivate boat slip (up to 25’; reserve in advance) with shore power, water hookup, dock ladder & fish cleaning stationbrbrWalk-down launch area for kayaks and paddleboardsbrbrResort-style oceanfront pool and outdoor showerbrbrPet-friendly with prior approvalbrbrFast Wi-Fi, Smart TVs, Keurig with coffee pods, washer/dryer, hotel-quality linens and towelsbrbrGated community with quiet hours (10 PM–9 AM) and lush, tropical landscapingbrbrWalk to 7+ restaurants, bars, coffee shops, and local shopsbrbrClose to fishing charters, snorkeling tours, Robbie’s Marina, and paddleboard rentalsbrbrKnow Before You Go:br7-night minimum staybrbrMaximum 2 vehicles (1 in garage, 1 in driveway)brbrTrailer parking available with advance noticebrbrNo boat launching on-sitebrbrNo glass in the pool areabrbrWhether you're here to fish, paddle, explore, or simply unwind, this Islamorada townhouse is the ideal home base for your next boating vacation, family getaway, or romantic retreat.brBook your stay at Peaceful Palms today—where sunrise views, dock days, and lasting memories await.

Bed

Bath

Sleeps

$226.76

/ Nightly

Condo

This condo is located in one of Islamorada's most prestigious condo complexes.

Islamorada, Florida, United States

PROPERTY NAME: Beacon Reef #307br83201 Old Highway, Islamorada, FloridabrbrLOCATION: Ocean side CondobrbrMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedbrMILE MARKER: 83.2brbrDETAILS: This like-new 2 bedroom/2 bath condo has fabulous ocean views and was totally remodeled/updated very recently. You'll love the sparkling new natural stone counter-top kitchen with stainless steel appliances, induction cook top and microwave. The interior is bright, fresh and airy. The furnishings are comfortable and inviting. Dine at the glass top table or pull up a stool to the kitchen counter while grabbing a snack. Store up to 32 bottles of your favorite wines in the dual-zone wine cooler. Relax on the private balcony, gazing at the ocean or sunrise. Both bathrooms have been completely remodeled and all linens needed are provided. The oversized master suite offers a king bed, wide ocean views, separate entrance to the balcony and a huge bath with walk-in shower. The guest bedroom provides spacious accommodations for friends and family. You'll love the ease and convenience of your own new washer/dryer and secured Wi-Fi. Two large flat screen TV's means you'll want for nothing in this captivating condo. Maximum number of guests is 4. brbrBeacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your own private balcony overlooking acres of lush tropical landscaping and gazing at the magnificent ocean views. Gather your ration of Vitamin D by simply lounging next to the free form swimming pool. Dock your boat in the marina. Dockage is first-come. Jet Skis and PWC are not permitted. Fillet your fish at the fish cleaning station. Exercise in the fitness center. Indulge your aching muscles by soaking them in the spa hot tub after a hard day of fishing, diving or snorkeling - or anytime that suits your fancy! This property is professionally managed by Keys Holiday Rentals. brbrSLEEPING ARRANGEMENTS: Sleeps 4 MaxbrPrimary Bedroom: King Bed Bathroom with ShowerbrGuest Bedroom: King Bed Bathroom with ShowerbrbrAMENITIES INCLUDE: Condo has community pool/hot tub, Indoor community space, outdoor BBQ, and gymbrbrACTIVITIES: Beach, Swimming, Boating, Offshore Fishing, On Shore Fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours and Culinary Adventures.brbrENHANCED CLEANING, DISINFECTION AND SANITIZATION: Our number one priority is the wellbeing and safety of our guests. We have contactless check-ins and check-outs. Our properties are cleaned and sanitized by professionally trained and equipped housekeepers who provide quality service, security and personal accountability. We use CDC housekeeping protocols, approved disinfectants and personal protection equipment. Our properties are private, well maintained, hygienic and sanitized. A whole safe and private space just for you and your family. brbrRESERVATIONS ARE NOT CONFIRMED UNTIL THE REQUIRED CONDOMINIUM ASSOCIATION APPLICATION IS APPROVED.

Bed

Bath

Sleeps

$571.87

/ Nightly

Private Vacation Home

A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool

Islamorada, Florida, United States

''BEAUTIFUL BAY-FRONT PROPERTY!!!!'' NEW POOL Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 10. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath.brEntire house has been remodeled, fully furnished, with a 90 ft Dock. Bring your clothes, boat, fishing and dive gear. Located in desirable Islamorada where you will have easy access to some of the best back-country fishing, and or ocean fishing which would include all of the paddle boarding, snorkeling, and diving that anyone would ever want, just minutes from Channel 5 and channel 2. Dog beach is 3 min away by boat. You will love the back porch outdoor living space which includes your own Bar over looking the water. This is a Boating, Fishing Scuba Diving/Snorkeling Paradise.brbrHouse, 3 Bedrooms, 2 Baths, Sleeps 10brbr213 Tollgate Blvd., Islamorada, Florida Keys mile marker 73 bay side, located 88 miles south of Miami International Airport and 71 miles North of Key West. It has three bedrooms, two bath, private home totally remodeled in late 2019, 90 foot dock, bay side with easy access to ocean.brbrFeatures: washer, dryer, gas BBQ, charcoal BBQ, hammock, ice freezer, ice maker, Outside Bar, fish cleaning table, tropical foliage, TV in living room, DVD, laminate floors, nautical ceiling fans throughout, central air conditioning, wireless high speed internet, all the amenities and conveniences of home in this one of a kind rental in the fabulous Florida Keys.brbrNo smoking inside the house please.brbrI purchased this house after renting in the Keys for many years, I got tired of looking so hard for good quality, clean hotels to rent which were and are still very difficult to find. If you are looking for something 'nice' that the actual house looks 'better' than the pictures, that will provide for your family and friends a vacation where memories will be made, that will last a lifetime and that is clean inside-out, then this is your rental.brbrFor further information or questions, contact owner manager ,brbrUnique BenefitsbrbrThis is my only vacation house , I live only 2 hours away and I take care of the house as good as our main home. brbrThis is my Happy Place, Piece of Paradise and I use the house personally when it isn't being rented, I spare no expense to keep it up and maintain it.brbrWhy die hard fishing and diving people love it-brIt is on the Bay, very close ocean access. brbrArea Information:brbrIslamorada is the sport fishing capital of the world. I am located in Tollgate Shores subdivision on the bay-side.brbrAttractions Within a Short Distance:brbrAnne's beach is just south if of us the ocean side, it is a public beach where you usually find a lot of wind surfers.brbrMobil grocery store and cafeteria is just north of the entrance of our subdivision and it is a local for purchasing certain groceries and food, very convenient.brbrFavorite Places To Eat:brbrHabanos , Cuban restaurant and Caloosa Cove marina Oceanside just across from my subdivision. brbrRobbie's, eat outside by the water or inside, local place very typical of Keys.brbrLazy Days, 3 miles north next to Bud and Mary's marina. Lunch and dinner, great local favorite place, large portions always good food and fresh fish. Reasonable prices. sit outside or inside. Terrific when there is a full moon coming up on the ocean side.brbrGreen Turtle, north on the ocean side, sit inside, nice elegant restaurant excellent. Breakfast, lunch and dinner.brbrMidway Café, north, breakfast and lunch favorite. Great coffee , pastries etc.brbrChef Michael, north, dinner, excellent, nice, fresh fish, quality.brbrMangrove Mike's , north, local favorite for breakfast, very Keys oriented. Serves lunch too. Not fancy.brbrZiggie & Mad Dogs, north, real nice dinner restaurant, steaks and seafood, quality, nice ambiance.brbrBayside Gourmet, north, great lunch and dinner, not fancy, but great food and reasonable, family style. brbrSquare Grouper, north on the bayside in Islamorada marina. Excellent, my favorite for dinner.

Bed

Bath

Sleeps

$379.2

/ Nightly

Private Vacation Home

Beautifully remodeled roomy single family stilt home,

Islamorada, Florida, United States

PROPERTY NAME: West Plaza br63 West Plaza Del Lago, Islamorada, FLbrbrLOCATION: Bayside HousebrbrMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedbrbrMILE MARKER: 74.5brbrDETAILS: West Plaza Del Lago will steal your breath away the moment you pull into the drive way. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter the home there is a charming foyer which leads to the spacious open concept living area with vaulted ceilings. On the right the kitchen, straight ahead the dining area and on the left the living area with a L shaped sofa. The fully equipped kitchen features stainless steel appliances and two breakfast/snack bars for casual dining - one by the sink area with bar stools and one with pull out saddle benches tucked under the granite counter top peninsula. For more formal dining there is a table which comfortably seats 6 people. In the living area a large wall mounted flat screen TV for your TV viewing pleasure. The two bedrooms are located just off the living area - one on the west side of the house and one on the east side - both have a wall mounted flat screen TV. The master suite has a king bed and ensuite bath with gorgeous tiled bath and large stall shower. The guest bedroom offers sleeping accommodation for three with two twin beds and a trundle. A full bath with tub/shower combination is adjacent. In addition to all the appealing features of this home there is an amazing sun room with a wall of windows overlooking the back yard, dock and canal. brbrOutside there is a 60' dock with boat lift and a fish cleaning station with water and electricity. The lift will accommodate a fully loaded boat up to 12,000 pounds. There is no additional charge for use of the boat lift, however adjustments to the bunks will be at guest expense by the company that services the lift. There is a table and chairs for relaxing outside along with three kayaks for your use - two singles and one double. Guest will have use of the garage for storing toys and use of the two freezers - one for bait only and one for food. There is a separate laundry area with a full sized washer and dryer. Wi-Fi is included. There's a gorgeous private sandy beach available only to residents of the Port Antigua neighborhood. The private sandy beach located directly on the bay offers oasis areas with BBQ grills and swaying palm trees. Bring your chair or blanket and enjoy the gentle tropical breezes. This is your opportunity to spend time in the Keys. Call or email immediately to make your reservations. This property is professionally managed by Keys Holiday Rentals. brbrSleeping Arrangements: Sleeps 5 comfortablybrPrimary Bedroom: King, Ensuite Shower/ Tub CombobrGuest Bedroom: 2 Twins + Trundle, Shower/ Tub CombobrbrAmenities Include: Dockage for up to a 35ft boat, kayaks, outdoor seating, BBQ grill. Sunroom seatingbrbrActivities: Beach, Swimming, Boating, Offshore Fishing, On Shore Fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours and Culinary Adventures.brbrENHANCED CLEANING, DISINFECTION AND SANITIZATION: Our number one priority is the wellbeing and safety of our guests. We have contactless check-ins and check-outs. Our properties are cleaned and sanitized by professionally trained and equipped housekeepers who provide quality service, security and personal accountability. We use CDC housekeeping protocols, approved disinfectants and personal protection equipment. Our properties are private, well maintained, hygienic and sanitized. A whole safe and private space just for you and your family.

Bed

Bath

Sleeps

$210.0

/ Nightly

Condo

Islamorada Spectacular Vacation At Executive Bay Club

Islamorada, Florida, United States

Come, Enjoy and Relax in our beautiful piece of the paradise in the Florida Keys. The Executive Bay Club is located in Islamorada, the Diving/Snorkeling and Sport Fishing Capital of the world! This is a private, gated community with 24 hour security and easy accessible parking. The grounds have 2 tennis courts, heated swimming pool, club house, private beach and fishing dock. brbrOur two story unit has been renovated. The master bedroom has a king size bed, a renovated bathroom is adjacent. The second bedroom has 2 queen size beds and its own newly renovated bathroom television and DVD player. Downstairs relax in our living room, that sports a big screen TV or enjoy the quite patio right outside. There is also a dining area, kitchen with full size dishwasher, microwave, refrigerator and washer and dryer and an additional renovated bathroom with shower. The unit is fully furnished and we provide cooking utensils, dishes, linens and towels. However, bring you own pool/beach towels.brbrNext door is Founders Park, known to be one of the Keys most beautiful parks, with baseball, soccer fields, exercise equipment, basketball courts, tennis courts and pros available for tennis drills, lessons and round robins, private beach and playground, boat marina and public boat ramp. Let's not to forget the heated Olympic size pool with diving and lap areas, where swim lessons are available. Minutes away are your charter boats and captains, your scuba and snorkeling trips and wind sailing lessons. Our water is clear and our reefs are impressive! Don't forget to stop by the local art galleries, 'Theater of the Sea', a Marine Adventure where you can swim with the dolphins or drop by the Diving Museum. The activities are plentiful... water sports, kayaking, jet skis, parasailing, boating, sunset cruises and just reading and relaxing on the beach! The restaurants are the best in the Keys with local fish served daily. brbrSorry No Pets or Nor SmokingbrbrSo come, relax and Enjoy whatever your pleasure may be!brbr

2

Bed

3

Bath

6

Sleeps

$466.89

/ Nightly

Private Vacation Home

Ocean View : OCEAN VIEW: POOL: ELEVATOR: PET FRIENDLY: GOLF CAR: HOME OFFICE

Islamorada, Florida, United States

✨ OCEAN VIEWS • POOL • ELEVATOR • PET FRIENDLY • GOLF CART • BEACH • GYM • HOME OFFICE ✨ brbrFREE CLEANINGbrbr OCEAN VIEWS AS FAR AS THE EYE CAN SEE! brWelcome to THE CASTAWAY 2 — your private island-style escape in beautiful Islamorada! This luxury 2-bedroom retreat comfortably sleeps up to 8 guests and is designed for ultimate relaxation, convenience, and unforgettable memories brbr DON’T LIKE STAIRS NO PROBLEM!br✔️ Private ELEVATOR + mobility lift = easy access for everyone brbr ️ LUXURY LIVING AT ITS FINESTbr✨ Fully furnished with designer touches throughoutbr Just bring your bags — everything else is ready for you!br Fully stocked kitchen for home-cooked mealsbr ️ Spacious bedrooms + ample closet spacebrbr ENTERTAINMENT EVERYWHEREbr 75” Smart TV in the living roombr 55” Smart TVs in each bedroom + upstairs loungebr Perfect for movie nights after a day in the sun!brbr WORK FROM PARADISE br✔️ Ergonomic sit/stand deskbr✔️ 22” monitor + wireless printer/scannerbr✔️ Fast WiFi so you can Work • Stay • Play seamlesslybrbr ️ RESORT-STYLE AMENITIES (YOU GET IT ALL!)brLocated in the highly social, oceanfront Sun Outdoors community brbr Heated pool (winter) + chilled pool (summer!)br ️ Private beach + loungersbr PET FRIENDLY! Dog beach just 100 steps away! br 3 Oceanside fireplacesbr Live music at the pool & beachbrbr ‍♀️ ADVENTURE AWAITS!br FREE kayaks + paddleboardsbr⚓ 46-slip marina (guest rates available)br Explore the stunning Florida Keys waters!brbr CRUISE IN STYLEbr FREE 4-person luxury golf cartbrZip around the community to the pool, beach, gym & more!brbr ️‍♂️ FUN + FITNESS + COMMUNITYbr Private gym accessbr Weekly cornhole tournamentsbr Oceanfront lawn & social areasbrbr⭐ TRUSTED HOSTS YOU CAN COUNT ONbr 165+ FIVE-STAR REVIEWS across platformsbr Long-time Keys residents & experienced hostsbrbr WHY YOU’LL LOVE ITbrThis brand-new 2025 home combines the privacy of your own space with resort-level amenities that rival the best in the country.brbr STAY LONGER, SAVE MORE!brAsk us about multi-month discounts brbr THE CASTAWAY 2 ISN’T JUST A STAY… IT’S AN EXPERIENCE.br Book now and start living your Florida Keys dream! ✨

Bed

Bath

Sleeps

$591.78

/ Nightly

Private Vacation Home

ISLAMORADA BEACH HOUSE

Islamorada, Florida, United States

Luxury Waterfront Home in Exclusive Port Antigua – Islamorada, FLbrbrEscape to this stunning 4,200 sq. ft. waterfront retreat in the coveted Port Antigua neighborhood of Islamorada, Florida. With breathtaking sunrises from two expansive terraces, this 5-bedroom, 4-bathroom home comfortably accommodates up to 10 guests—perfect for families or groups seeking a serene getaway.brbrFeatures and Amenities:br • Spacious 5 bedrooms and 4 bathrooms, ideal for up to 10 guests.br • Two large terraces offering stunning ocean views.br • Access to a private community boat ramp for easy exploration of the Florida Keys.br • Prime location near top attractions, shops, and restaurants.brbrNearby Attractions:br • 5 minutes to Robbie’s of Islamoradabr • 10 minutes to Bass Pro Shops – World Wide Sportsmanbr • 10 minutes to Publix Super Marketbr • 15 minutes to Theatre of the Seabr • 30 minutes to the famous Seven Mile Bridgebr • 30 minutes to MillionAir Private AirportbrbrEnjoy luxury living in Islamorada with all the comforts of home.brbrContactbrCall 786-227-3354 to schedule a showing or book your stay today!

Bed

Bath

Sleeps

$2777.65

/ Nightly

Private Vacation Home

Peninsula Villa | Boat Dock | Heated Pool | Sunset Point

Islamorada, Florida, United States

5

Bed

4

Bath

12

Sleeps

Vacation Rentals By Owner In Islamorada, FL

$660.31

$483.81

$483.81

$434.25

$434.25

$974.21

$660.31

$660.31

$483.81

$434.25

$2145.49

$650.15

$748.56

$226.76

$571.87

$379.2

$210.0

$466.89

$591.78

$2777.65

Rent a place that suits your needs

Most popular vacation rentals in Islamorada

$2110.32

$2171.25

$2241.97

$2531.12

$2777.65

$2859.73

$3453.41

$4417.51

$1107.85

$981.86

Most Popular Cities in Florida