Islamorada, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Islamorada, Florida on RentalSaver.com!

Islamorada Rentals

From $714 per night (USD)
VRBO
Snorkeling & Kayaking Beach Resort! Seaside Villa w/Patio! Marina, Parking
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $714 per night (USD)
VRBO
From $892 per night (USD)
VRBO
Your Home Away From Home! 4 Relaxing Units, FREE Parking, Onsite Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $892 per night (USD)
VRBO
From $714 per night (USD)
VRBO
Snorkeling & Kayaking Beach Resort! Seaside Villa w/Patio! Marina, Parking
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $714 per night (USD)
VRBO
From $555 per night (USD)
VRBO
Convenient Location! 3 Convenient Units, Pool, Pet-Friendly, Free Parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $555 per night (USD)
VRBO
From $442 per night (USD)
VRBO
Pets are Allowed Here! 2 Comfortable Units, Free Breakfast, Parking, Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $442 per night (USD)
VRBO
From $442 per night (USD)
VRBO
Escape The Hustle and Bustle! 2 Classy Units, Free Parking, Onsite Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $442 per night (USD)
VRBO
From $892 per night (USD)
VRBO
Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $892 per night (USD)
VRBO
From $347 per night (USD)
VRBO
108 Anglers Reef Islamorada 31' BOAT SLIP AVAILABLE
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful Key West Style home 2 BR 2 BA (en suites) + 1 HF BA Sleeps 6 Islamorada Vacation rental #24-3018 108 Anglers ...
From $347 per night (USD)
VRBO
From $516 per night (USD)
VRBO
Feel the breeze of the keys
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
**HOUSE HAS BEEN RENOVATED AND PICTURES TO COME** Perfect Vacation Home in Islamorada, the center of the Keys Island. T ...
From $516 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Best Location in Islamorada!! Beach access - Boat trailer parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Gorgeous and highly appointed luxury Island villa with beach access. You are right in the middle of it all with this per ...
From $267 per night (USD)
Expedia
From $399 per night (USD)
VRBO
The Nest Villa & Marina with boat ramp, sun terrace, water views. Pet friendly!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
If you are looking for peace and tranquility or somewhere to launch and dock your boat for the best fishing and diving i ...
From $399 per night (USD)
VRBO
From $205 per night (USD)
VRBO
Coconut Palm Inn Beachfront Hideway's Harborview House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3 bedroom, 2 bathroom Key Largo vacation rental's layout is a perfect setting to enjoy the Florida Keys on your ter ...
From $205 per night (USD)
VRBO
From $423 per night (USD)
VRBO
Islamorada Oasis, Luxurious 4 bedroom 3 bath home. Heated pool! Boat Lift option
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Islamorada Oasis is designed for families and outdoor lovers! Inside and out, its ready for entertaining and keys styl ...
From $423 per night (USD)
VRBO
From $199 per night (USD)
Expedia
Mercy’s waterfront piece of paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our home is a unique place situated in the best location in the mid/upper keys. A single family property, all refurbishe ...
From $199 per night (USD)
Expedia
From $1046 per night (USD)
VRBO
The Villa by the Bay, Islamorada FL private plunge pool, boat dockage & sunsets
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Take your heart, family & fishing gear to the blissful Villa by the Bay! Quaint gated 8 homes; Coral Cove is centrally l ...
From $1046 per night (USD)
VRBO
From $421 per night (USD)
VRBO
Fantastic Bayside Townhouse
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Fantastic gated Bayside townhouse with all the bells and whistles. Excellant location with everything you need to have a ...
From $421 per night (USD)
VRBO
From $192 per night (USD)
VRBO
Zesty Lower Matecumbe Condo with Private Beach & Dockage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
It's not every day that you come across a rental like this. This delightful and fun 2 bedroom, 1.5 located in Lower Mate ...
From $192 per night (USD)
VRBO
From $478 per night (USD)
Expedia
Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Tucked away in the vibrant Florida Keys, is our pristine Bungalow paradise. We are located in the heart of Islamorada, w ...
From $478 per night (USD)
Expedia
From $201 per night (USD)
VRBO
Keys Getaway – 2 Bikes, Heated Pool, Small Beach & Sunset Dock Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to Your Florida Keys Getaway – A Slice of Paradise in Islamorada Welcome to our beautiful 2-bedroom, 2-bathroom t ...
From $201 per night (USD)
VRBO
From $603 per night (USD)
VRBO
Immaculate Islamorada Home with 100' of Dockage, Pool & More!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This tropical oasis has everything you need and more for the perfect summer vacation! Nestled in the highly sought-aft ...
From $603 per night (USD)
VRBO
From $550 per night (USD)
VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $550 per night (USD)
VRBO
From $377 per night (USD)
VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $377 per night (USD)
VRBO
From $550 per night (USD)
VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $550 per night (USD)
VRBO
From $377 per night (USD)
VRBO
Prime Location! Onsite Pool, Free Breakfast, Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $377 per night (USD)
VRBO
From $548 per night (USD)
VRBO
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $548 per night (USD)
VRBO
From $376 per night (USD)
VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $376 per night (USD)
VRBO
From $456 per night (USD)
VRBO
Keys waterfront paradise
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Beautiful keys oceanfront home fully equipped . great for entertainment. fishing paradise just a short distance from wor ...
From $456 per night (USD)
VRBO
From $468 per night (USD)
Expedia
Best location in downtown Islamorada. 2 Houses with Beach access!
Bedrooms:
5
Bathrooms:
6
Sleeps:
18
Unbelievable location in Islamorada Florida Keys! You have beach access and boat trailer parking. This listing is for 2 ...
From $468 per night (USD)
Expedia
From $178 per night (USD)
VRBO
OCEAN FRONT TOWN HOUSE with breath taking views from all 3 balconies.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We are delighted to offer this 2 bedroom, 1 1/2 bathrooms OCEANFRONT TOWNHOUSE!!! Breathtaking views off of all 3 balco ...
From $178 per night (USD)
VRBO
From $568 per night (USD)
VRBO
Amazing 4 Bedroom Canal Home with Pool and Dockage-Holly's Hideout by FKLR
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Canal Front......Pool......Dockage......Pet friendly......It’s all here at Holly's Hideout! Located in beautiful Tave ...
From $568 per night (USD)
VRBO
From $3453 per night (USD)
VRBO
10 Bedroom Private Ocean Front Estate
Bedrooms:
10
Bathrooms:
10
Sleeps:
22
The Island Palm Estates is a newly constructed estate that includes 2 separate, luxurious homes with all the modern conv ...
From $3453 per night (USD)
VRBO
From $438 per night (USD)
VRBO
Pet Friendly 2 Bedroom in Venetian Shores Sleeps 10
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
The Salty B is located in the popular neighborhood of Venetian Shores! Canal front home on Snake Creek gives you fast ac ...
From $438 per night (USD)
VRBO
From $383 per night (USD)
VRBO
Fabulous Island Getaway! Easy access to Florida Bay, Private Beach, Elevator
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Enjoy watching the ospreys and manatees from the dock at this beautiful Port Antigua home on Biscayne Blvd. You have acc ...
From $383 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Keys Villa--Islamorada private beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Two bedroom "gem" in the Florida Keys!! Enjoy our sand beach, beautiful sunsets, fish from our docks, swim in our pool, ...
From $288 per night (USD)
Expedia
From $869 per night (USD)
VRBO
Maison Matecumbe.... the heart of Islamorada!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Maison Matecumbe #301 - Maison Matecumbe is an exclusive gated and private boutique complex comprised of 9 units. Centra ...
From $869 per night (USD)
VRBO
From $184 per night (USD)
VRBO
Charming Condo in Paradise!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Take a break & unwind at this charming Islamorada gem! Let this 1/1 bright & homey condo be your needed getaway to parad ...
From $184 per night (USD)
VRBO
From $272 per night (USD)
VRBO
Tropical Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful bayside villa in Islamorada. Sandy beach, fishing dock, pool, tennis court and boat slip for up to 25 ft boat ...
From $272 per night (USD)
VRBO
From $602 per night (USD)
VRBO
Venetian Shores 20K boat lift 28 day Minimum, ...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Venetian shores 4 bedroom 3 bath, pool, hotub, 300lbs ice machine with 20K boat lift, Master has a double walk-in shower ...
From $602 per night (USD)
VRBO
From $206 per night (USD)
VRBO
Beautiful 2 Bedroom 2 Bath Condo Coral Harbour Islamorada - Marina, Pool, Gated
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This special place is close to everything, making it easy to plan your visit. Beautiful updated 2 bedroom 2 bath watervi ...
From $206 per night (USD)
VRBO
Click For Pricing
Expedia
A place in paradise!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This unique home gives you the quintessential keys experience. Nestled in a small, quaint gated, private community with ...
Click For Pricing
Expedia
From $527 per night (USD)
VRBO
New Rental! Beautiful canal pool home with dockage!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Cozy, canal front, pool home at MM 74 in Islamorada's desirable Port Antigua (Lower Matecumbe Key) with quick Florida Ba ...
From $527 per night (USD)
VRBO
Click For Pricing
Expedia
PARADISE FOUND! 3 BD townhome in BEACHFRONT Executive Bay Club in Islamorada, FL
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Paradise Found! Enjoy fantastic sunsets in an updated 1400 sq. ft. townhouse in beautiful Executive Bay Club, on mile ma ...
Click For Pricing
Expedia
From $485 per night (USD)
VRBO
Mojito Breeze Getaway
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Beachy but elegant, close to mainland FL, sleeps 12 comfortably, timeless tropical getaway, plenty of room Nice, quiet ...
From $485 per night (USD)
VRBO
From $1182 per night (USD)
VRBO
The Sailfish House ~ 4 Bed / 4 Bath Luxury Oceanfront Home in Islamorada!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to the “Sailfish House” at Tarpon Point! Soak up the sun and take in the spectacular views at this opulent 4 be ...
From $1182 per night (USD)
VRBO
From $508 per night (USD)
VRBO
4BR waterfront home with POOL, boat slip with straight shot to Alligator Reef!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Island Villa Rental Properties offers Seas The Day in Islamorada, Florida Keys. Seas the Day is a fun, 4 bedroom house ...
From $508 per night (USD)
VRBO
From $759 per night (USD)
VRBO
Venetian Shores 5BR/7BA Home with Pool, Spa & Boat Lifts
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Rare Summer Openings! Your Private Resort Awaits in Islamorada If you’ve been dreaming of an island escape with all th ...
From $759 per night (USD)
VRBO
From $405 per night (USD)
VRBO
Islamorada Key Waterfront House w/ Private Boat Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Cozy 2/2 Waterfront home located in the Best Location. Two King beds . High speed Wifi, Smart TVs, BBQ, Great living r ...
From $405 per night (USD)
VRBO
From $771 per night (USD)
Expedia
ISLAMORADA DREAM HOUSE
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
ONE-OF-A-KIND VACATION EXPERIENCE. You will never want to leave. Large open space, dining, kitchen and living room. Priv ...
From $771 per night (USD)
Expedia
From $208 per night (USD)
VRBO
New to the Market: Summer Sea 207
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summer Sea Condo #207: Modern and spectacularly updated 2nd floor unit with private balcony just steps away from the sta ...
From $208 per night (USD)
VRBO
Click For Pricing
Expedia
Bay view villa in Islamorada, palm trees, shade trees and two private porches
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Unwind with a Bay view, approx. 1 hour from Miami airport. Access to mini beach, great sunsets and boat ramp, swimming ...
Click For Pricing
Expedia
From $218 per night (USD)
VRBO
This condo is located in one of Islamorada's most prestigious condo complexes.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
PROPERTY NAME: Beacon Reef #307 83201 Old Highway, Islamorada, Florida LOCATION: Ocean side Condo MINIMUM STAY: 28 Day ...
From $218 per night (USD)
VRBO
From $340 per night (USD)
Expedia
Beautifully remodeled roomy single family stilt home,
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
PROPERTY NAME: West Plaza 63 West Plaza Del Lago, Islamorada, FL LOCATION: Bayside House MINIMUM STAY: 28 Days, All s ...
From $340 per night (USD)
Expedia
From $351 per night (USD)
VRBO
Beautiful Water Views from every room in the House
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
PROPERTY NAME: Harbor House 101 San Juan Dr., Islamorada, FL LOCATION: Bayside Canal home located in the Upscale Veneti ...
From $351 per night (USD)
VRBO
From $624 per night (USD)
Expedia
Beautiful house located in the prestigious neighborhood of Port Antigua on a deep, wide canal.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
PROPERTY NAME: Pelican Landing 60 West Plaza Del Lago, Islamorada, FL LOCATION: Bayside Private Home in the neighborhoo ...
From $624 per night (USD)
Expedia
From $382 per night (USD)
VRBO
Charming Angler's Reef Home with Pool, Dock, Beach & Ocean View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to Islamorada’s Finest Oceanfront Gated Community Soak up the sun and enjoy the ocean breeze from this charming ...
From $382 per night (USD)
VRBO
From $680 per night (USD)
Expedia
Boaters Paradise - Luxury Islamorada waterfront home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Stunning waterfront Islamorada house on a corner lot with direct access to the Bay and 5 minutes from the Atlantic Ocean ...
From $680 per night (USD)
Expedia
$\Our Happy Place\ Paradise in Islamorada with Heated Pool and 90 ft Dock$
From $496 per night (USD)
VRBO
\"Our Happy Place\" Paradise in Islamorada with Heated Pool and 90 ft Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Located in the desirable Islamorada which is know as the “Sportfishing Capital of the World” and where you will find the ...
From $496 per night (USD)
VRBO
From $286 per night (USD)
VRBO
Bayside Boater's Paradise-great for Snowbirds-60 d min stay- add 1:1private unit
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
This 2 bedroom- 2 bath, fully-equipped kitchen waterfront home on a deep canal offers a 75 ft-wide frontage dock with 38 ...
From $286 per night (USD)
VRBO
From $760 per night (USD)
VRBO
Venetian Shores 5BR/7BA Home with Pool, Spa & Boat Lifts Open Sept. 2025
Bedrooms:
7
Bathrooms:
5
Sleeps:
10
Rare Summer Openings! Your Private Resort Awaits in Islamorada We’ve just had a rare cancellation at one of our most s ...
From $760 per night (USD)
VRBO
From $1684 per night (USD)
VRBO
Ocean & Pool Front Maison Residences, on sandy beach, heated pool in Islamorada
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
FLORIDA KEYS BEACHFRONT VACATION RENTALS AT MAISON RESIDENCES While staying at the Maison Residences, you’ll have the c ...
From $1684 per night (USD)
VRBO
From $133 per night (USD)
VRBO
Cute Studio in Summer Sea Condominium
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This cute apartment is new to the rental market. Modern and clean with all the comforts of home with tropical décor, lig ...
From $133 per night (USD)
VRBO
From $440 per night (USD)
Expedia
3 Bedroom Islamorada Condo w/ 30' Boat Slip & Ocean Views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Mother Ocean! This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfec ...
From $440 per night (USD)
Expedia
From $692 per night (USD)
VRBO
Why watch the Sunrise when you have a Mangrove Sunset
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This stunning pool home is nestled along a private canal with convenient dockage and quick access to the bay! This lu ...
From $692 per night (USD)
VRBO
From $649 per night (USD)
Expedia
Lush tropical plantings in a gated compound located directly on the Florida Bay
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
PROPERTY NAME: Little Bay Cottage 82246 Overseas Highway, Islamorada, Florida LOCATION: Cottage located directly on th ...
From $649 per night (USD)
Expedia
From $447 per night (USD)
VRBO
Port Antigua Waterfront Home With Private Beach Access
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This Keys Home is Located in Beautiful Port Antigua. 4 Br/ 3 Ba Sleeps 8 Comfortably. All Rooms Have Queen Sized Beds. L ...
From $447 per night (USD)
VRBO
From $462 per night (USD)
VRBO
Cozy Islamorada retreat!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Our Islamorada home is your home away from home! Our home is in a private and quiet, gated community on the bay side, w ...
From $462 per night (USD)
VRBO
From $671 per night (USD)
VRBO
Best Place to Unwind! 2 Spacious Units, Free Breakfast, Swimming Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $671 per night (USD)
VRBO
From $333 per night (USD)
VRBO
Tropical Paradise Retreat in Islamorada! Pool, Pet-friendly, Free Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $333 per night (USD)
VRBO
From $331 per night (USD)
VRBO
Comfort and Convenience! Swimming Pool, Free Parking, Pets Allowed!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $331 per night (USD)
VRBO
From $333 per night (USD)
VRBO
Relax and Recharge! Pets Allowed, Outdoor Swimming Pool, Free Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $333 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Cozy Islamorada home! Pet-Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to this beautiful and Newley renovated cozy Islamorada home! This home is a couple blocks away from the famous A ...
From $319 per night (USD)
VRBO
From $130 per night (USD)
VRBO
Pool, Beach and Tennis Court! Fishing, swimming and relaxation!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Take it easy at this unique and tranquil getaway. Enjoy this well equipped 2 bedroom, 2 bath home. Enjoy beautiful suns ...
From $130 per night (USD)
VRBO
From $7046 per night (USD)
VRBO
Island Beach House Oasis Your Memory Maker awaits
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
***Notwithstanding anything in the rates page the minimum renal is 28 days*** There is luxury, luxury and unrivaled, an ...
From $7046 per night (USD)
VRBO
From $381 per night (USD)
VRBO
Newly renovated Port Antigua canal front home with convenient dockage!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Fall Special Rates!! Discounted rates through December, inquire within! Welcome to your dream vacation getaway in the ...
From $381 per night (USD)
VRBO
From $545 per night (USD)
VRBO
Canal front home in Venetian Shores. Perfect for families . A boater's paradise!
Bedrooms:
3
Bathrooms:
3
Sleeps:
16
This canal front home is located in the prestigious Venetian Shores neighborhood. The perfect location right off of Snak ...
From $545 per night (USD)
VRBO
From $595 per night (USD)
Expedia
Cozy canal in the Keys - leads directly into crystal blue ocean! 🌊
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
A 75' bulkhead on the main exit channel 3 houses from the bay. Private boat slip in the neighborhood you can put your ow ...
From $595 per night (USD)
Expedia
From $509 per night (USD)
VRBO
La Casita White Marlin
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to this stunningly renovated 5-bedroom, 3-bathroom home situated on a picturesque canal, offering a seamless ble ...
From $509 per night (USD)
VRBO
$Tranquility Cove \nBeautiful Remodeled home in the heart of Islamorada.$
From $275 per night (USD)
Expedia
Tranquility Cove \nBeautiful Remodeled home in the heart of Islamorada.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
About this space This beautiful newly remodeled (99%) Completed , modern home sits in the middle of great restaurants, t ...
From $275 per night (USD)
Expedia
From $248 per night (USD)
VRBO
“ The Ultimate redneck” boat experience
Bedrooms:
0
Bathrooms:
1
Sleeps:
2
Are you ready for modern day pirate life ? Wonder how the locals live ? Well then we can show you ! Redneck paradise, Pr ...
From $248 per night (USD)
VRBO
From $216 per night (USD)
VRBO
Sandy Toes Await At This Beach Front Sandy Point Condo!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your perfect beachside retreat! Discover the epitome of relaxation and luxury in our meticulously renovated m ...
From $216 per night (USD)
VRBO
From $305 per night (USD)
VRBO
Ocean View Delight | Sea Gulls 310 ~ Monthly Rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Best View in the Keys - You will feel right at home in this beautifully renovated condo with FULL OCEAN VIEW. T ...
From $305 per night (USD)
VRBO
From $287 per night (USD)
Expedia
Islamorada Hidden Treasure
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy luxury in the Florida Keys in this private oasis at Coral Harbour. The property is equipped with a marina, fuel, ...
From $287 per night (USD)
Expedia
From $1316 per night (USD)
VRBO
Complete Duplex on Gated Bayfront Property
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
PROPERTY NAME: Little Bay Prime 82246 Overseas Highway, Islamorada, Florida LOCATION: Two story Duplex Located Directl ...
From $1316 per night (USD)
VRBO
From $657 per night (USD)
Expedia
2nd Floor Duplex on Gated Bayfront Property
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
PROPERTY NAME: Little Bay Upper Duplex 82246 Overseas Highway, Islamorada, Florida LOCATION: Upper Duplex located direc ...
From $657 per night (USD)
Expedia
From $1968 per night (USD)
VRBO
Entire Compound on Gated Bayfront Property
Bedrooms:
6
Bathrooms:
6
Sleeps:
18
PROPERTY NAME: Little Bay Compound 82246 Overseas Highway, Islamorada, Florida LOCATION: Cottage and Two Story Duplex ...
From $1968 per night (USD)
VRBO
From $658 per night (USD)
Expedia
Gated Estate Duplex on the Bay with dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
PROPERTY NAME: Little Bay Lower Duplex 82246 Overseas Highway, Islamorada, Florida LOCATION: Duplex located directly on ...
From $658 per night (USD)
Expedia
From $1146 per night (USD)
VRBO
Sandy Beach Cove🏝️🏖️ Gated Private Beach Home Plus Cottage Oasis , With Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Relax , Enjoy and Indulge yourself with Family and friends on this Over Half Acre Private Ocean Beach Oasis 🏝️🏖️ with ...
From $1146 per night (USD)
VRBO
From $190 per night (USD)
Expedia
Radiant waterfront retreat with remarkable views, patio, tennis court, & grill
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tollgate Tides Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $190 per night (USD)
Expedia
From $347 per night (USD)
VRBO
Islamorada waterfront villa
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Resort Style Venetian Shores Home with 70 ft Dock on a 100 foot wide canal Completely remodeled. Two Bedrooms with King ...
From $347 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Port Antigua Retreat on Canal with Boat Lift and Private Beach Access
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
This luxurious 4 bedroom, 3 bathroom house offers exceptional opportunity to experience the Florida keys in style with i ...
From $412 per night (USD)
Expedia
From $725 per night (USD)
VRBO
Tekeze ~ Relaxed Resort Style Home with 5 Bedrooms, Pool & Dockage
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Welcome to Tekeze! Short for "Take it Easy,” this oversized 5-bedroom, 4.5-bath home is located on a wide canal in the ...
From $725 per night (USD)
VRBO
From $1054 per night (USD)
Expedia
Islamorada Keys Waterfront Heated Pool Hottub Luxury Canal Home w Private Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Waterfront Islamorada 4/3 Deep Water Canal w direct easy access to ocean and bay with Amazing heated Pool and Hottub. ...
From $1054 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful Waterfront Townhome in Islamorada with Boat Slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Cozily furnished bayside townhome & boat slip (option to rent), located in desirable 'Futura Yacht Club' gated community ...
Click For Pricing
VRBO
From $360 per night (USD)
VRBO
Canal Front Oasis with Private Pool: Your Perfect Waterfront Getaway!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled within the prestigious Venetian Shores community, this captivating canal front duplex offers a remarkable blend ...
From $360 per night (USD)
VRBO
From $351 per night (USD)
VRBO
Newly Renovated Waterfront Home located in beautiful Islamorada with dockage.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Ready for your dream vacation? Newly remodeled and gated waterfront home located in the fishing capital of the world. T ...
From $351 per night (USD)
VRBO
From $555 per night (USD)
VRBO
Island Oasis in Islamorada: Your Private Paradise Awaits!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your ultimate Florida Keys dream getaway! This secluded home is perfectly located in the desired gated neighb ...
From $555 per night (USD)
VRBO
From $265 per night (USD)
VRBO
3 Bedroom Home in Islamorada with Private Dock, Boat Ramp & private beach access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Visiting a house in Islamorada is a dream come true for those in search of the ultimate tropical paradise. Nestled in th ...
From $265 per night (USD)
VRBO
From $473 per night (USD)
Expedia
Gorgeous Keys Vacation Home in Prestigious Neighborhood of Port Antigua
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Beautiful Port Antigua waterfront home with a 60 foot concrete dock on a wide, clear-water canal. Access to Port Antigu ...
From $473 per night (USD)
Expedia
From $279 per night (USD)
VRBO
Classic canal home with vintage charm!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect home away from home! In the heart of Islamorada, this Venetian Shores house is ideally located, ...
From $279 per night (USD)
VRBO
$Yolo \ You only live once\ - Fishing Paradise in Islamorada with a 70ft Dock!!!!$
From $339 per night (USD)
VRBO
Yolo \" You only live once\" - Fishing Paradise in Islamorada with a 70ft Dock!!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1440 sf - 2 Bedrooms king size bed in master bedroom with 2 queen beds in guest room (also includes xtra bed in guest ro ...
From $339 per night (USD)
VRBO

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