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

Islamorada Rentals

From $548 per night (USD)
VRBO
Ideal Mix of Comfort and Value! Onsite Pool, Free Parking, Pets Allowed
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $548 per night (USD)
VRBO
From $548 per night (USD)
Expedia
Experience Soothing Moments & Luxury! Free Parking, Onsite Pool, Pet-friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $548 per night (USD)
Expedia
From $831 per night (USD)
VRBO
Your Dream Escape in Islamorada! Pet-friendly Property, Swimming Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $831 per night (USD)
VRBO
From $418 per night (USD)
Expedia
Indulge in Home-Like Comfort! Free Parking, Onsite Pool, Pet-friendly Property
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $418 per night (USD)
Expedia
From $810 per night (USD)
VRBO
Relax and Recharge! 2 Comfortable Units, Free Parking, Onsite Swimming Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $810 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Short Distance From The Well Known Sites! Free Parking, Onsite Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $420 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Make Your Trip More Enjoyable! Onsite Pool, Pets Allowed, Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $383 per night (USD)
VRBO
From $340 per night (USD)
Expedia
Embrace the Sugar Rush Experience! Onsite Pool, Free Parking, Near Anne's Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $340 per night (USD)
Expedia
From $765 per night (USD)
VRBO
Charming Escape in Islamorada! 2 Modern Units, Swimming Pool, Pets Allowed!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $765 per night (USD)
VRBO
$Come Create Memories w\/ Fun-filled Adventures at this Paradise! Free Parking$
From $340 per night (USD)
Expedia
Come Create Memories w\/ Fun-filled Adventures at this Paradise! Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $340 per night (USD)
Expedia
From $382 per night (USD)
VRBO
Discover Islamorada's Treasures! Pets Allowed, Swimming Pool, Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $382 per night (USD)
VRBO
From $525 per night (USD)
Expedia
Your Tropical Home in Islamorada! Pets Allowed, Swimming Pool, Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $525 per night (USD)
Expedia
From $290 per night (USD)
VRBO
Charming 3-bedroom townhome in fabulous Islamorada seconds from the bay!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your home away from home in Islamorada with 3 bedrooms plus a loft. This cool townhome features a king bed, queen bed, 2 ...
From $290 per night (USD)
VRBO
$Charming 2\/2 in Islamorada - Private Access to White Marlin Beach$
From $290 per night (USD)
Expedia
Charming 2\/2 in Islamorada - Private Access to White Marlin Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This Islamorada house boasts 2 inviting bedrooms with 1 king bed and 2 queen beds. The spacious living room features a c ...
From $290 per night (USD)
Expedia
From $251 per night (USD)
VRBO
Charming 2-bedroom water-front home in Islamorada in the Florida Keys
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Florida Keys are waiting for you at this 2-bedroom water-front home. Nestled in a tranquil setting, this quaint prop ...
From $251 per night (USD)
VRBO
Click For Pricing
Expedia
Matecumbe Resort: Ocean View One Bedroom.Your Home Away From Home In The FL Keys
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Matecumbe Resort offers well-appointed, air-conditioned accommodations in Islamorada, renowned as the fishing capital of ...
Click For Pricing
Expedia
$2 BD\/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL$
Click For Pricing
VRBO
2 BD\/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience paradise like a local in this superb 2-bedroom 2 bath Villa with private patio and your own on premises boat ...
Click For Pricing
VRBO
From $319 per night (USD)
Expedia
Deep Water Home located in White Marlin Beach Neighborhood
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
PROPERTY NAME: Marlin House 156 Venetian Drive, Islamorada, FL 33036 LOCATION: Bayside Canal home located in the popula ...
From $319 per night (USD)
Expedia
Click For Pricing
VRBO
Matecumbe Resort: Seaview One Bedroom. Your Home Away From Home in the FL Keys.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Matecumbe Resort offers well-appointed, air-conditioned accommodations in Islamorada, renowned as the fishing capital of ...
Click For Pricing
VRBO
$Private Beach Ocean Front Oasis \/ Pickleball court \/ Heated Pool \/ Designated Paradise Key$
From $5442 per night (USD)
Expedia
Private Beach Ocean Front Oasis \/ Pickleball court \/ Heated Pool \/ Designated Paradise Key
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
Hidden in the heart of Islamorada, this oceanfront villa offers an unmatched privilege of a secluded private beach—an ex ...
From $5442 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Charming 3-bedroom condo with WiFi and AC in delightful Islamorada
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience Islamorada like a local in this 3-bedroom condo. This superb property features 2 queen beds and 2 bunk beds, ...
From $295 per night (USD)
VRBO
$Spacious & Remodeled condo w\/ sunset views!$
From $867 per night (USD)
Expedia
Spacious & Remodeled condo w\/ sunset views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
LIVE AND LOVE THE FLORIDA KEYS LIFESTYLE! Welcome to this stunning, fully remodeled condo in the highly sought-after Fu ...
From $867 per night (USD)
Expedia
From $300 per night (USD)
VRBO
BAY UNIT! 3-bedroom townhome in beautiful Islamorada with full amenities
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Stunning Bay-View Townhome in Executive Bay Club – Newly Renovated! Don't miss out on this rare gem! Perfectly located ...
From $300 per night (USD)
VRBO
From $933 per night (USD)
Expedia
Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish c ...
From $933 per night (USD)
Expedia
$Beach Residence \/ Private overwater dock \/ Heated Pool \/ Mahi Key$
From $2106 per night (USD)
VRBO
Beach Residence \/ Private overwater dock \/ Heated Pool \/ Mahi Key
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Relish ocean serenity in this residence set directly on a secluded beach, where an open-concept design seamlessly merges ...
From $2106 per night (USD)
VRBO
From $795 per night (USD)
Expedia
Beautiful Beach House directly ON the beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Islamorada Oceanfront home located directly on a private beach; enjoy swimming snorkeling, and ideal for kitesurfing! ...
From $795 per night (USD)
Expedia
$Ocean View Two Duplex Penthouses \/ Retreat amenities: tennis court, heated Pool | Vista Key$
From $1414 per night (USD)
VRBO
Ocean View Two Duplex Penthouses \/ Retreat amenities: tennis court, heated Pool | Vista Key
Bedrooms:
7
Bathrooms:
8
Sleeps:
24
Indulge in the epitome of coastal living in these two connected expansive duplex penthouses boasting ocean views in Isla ...
From $1414 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Flawless Newer Ocean Front Home in Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This newer home is sitting quietly behind a controlled access gate with a personal view of the Atlantic Ocean. Full two ...
From $280 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Charming 2-bedroom house in brilliant Tavernier near Marinas and Founders Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in Tavernier at this delightful house. This charming property features 2 bedrooms - one with a king bed and the o ...
From $235 per night (USD)
VRBO
From $237 per night (USD)
Expedia
Islamorada Tropical Paradise with New 40 Foot Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect getaway in beautiful Tavernier! This stunning vacation home offers the ultimate Florida Keys exp ...
From $237 per night (USD)
Expedia
$Perfect Vacation home, heated\/chilled pool, lots of dockage, private beach!!$
From $526 per night (USD)
VRBO
Perfect Vacation home, heated\/chilled pool, lots of dockage, private beach!!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
This fabulous house in Islamorada offers 5 bedrooms and 3 full bathrooms, heated/chilled pool, commerce ice machine, and ...
From $526 per night (USD)
VRBO
$Minutes to Library Beach Park! 2 Villa w\/ Living Area | Free Onsite Parking$
From $1422 per night (USD)
Expedia
Minutes to Library Beach Park! 2 Villa w\/ Living Area | Free Onsite Parking
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Start with your ultimate bayside getaway, located along the stunning coastline. Our idyllic resort offers a tranquil esc ...
From $1422 per night (USD)
Expedia
From $641 per night (USD)
VRBO
Reel Paradise, Islamorada
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Mile Marker 74 – Bayside, Canal front Canal-Front Retreat with Pool & Prime Dockage | Lower Matecumbe Key, Islamorada ...
From $641 per night (USD)
VRBO
From $152 per night (USD)
Expedia
Islamorada Haven -- FIshing, watersports, relaxation
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This beautiful Islamorada home has been newly renovated and ready for your Margaritaville vacation. Sitting on a major ...
From $152 per night (USD)
Expedia
$\Pressure Drop\ ~ 3 Bedroom \/ 2.5 Bath Condo with Ocean Views in Islamorada$
From $561 per night (USD)
VRBO
\"Pressure Drop\" ~ 3 Bedroom \/ 2.5 Bath Condo with Ocean Views in Islamorada
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Pressure Drop! This beautiful ocean-view condo features three bedrooms and two full bathrooms, making it an ...
From $561 per night (USD)
VRBO
From $177 per night (USD)
Expedia
Coastal Getaway at Plantation by the Sea
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to Islamorada and enjoy the laid-back lifestyle of the Florida Keys in this 2-bedroom, 2-bathroom condo at Planta ...
From $177 per night (USD)
Expedia
From $547 per night (USD)
VRBO
Bayfront Bliss in Islamorada, Private Dock & Stunning Sunset Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your laid-back bayfront retreat in the Indian Waterways neighborhood of Plantation Key! This spacious 3-bedro ...
From $547 per night (USD)
VRBO
From $363 per night (USD)
Expedia
Experience Waterfront Bliss at Futura Yacht Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your slice of paradise at Futura Yacht Club! This beautifully renovated 2-bedroom, 2-bathroom townhome offers ...
From $363 per night (USD)
Expedia
From $2171 per night (USD)
VRBO
NEW! Stunning Oceanfront Estate with Private Pool ~ Beach - 2026+ Calendar only
Bedrooms:
7
Bathrooms:
6
Sleeps:
14
License # 204. | ** 3 payment schedule available** | No Pet Charges | No security deposit | SATURDAY TO SATURDAY ONLY ...
From $2171 per night (USD)
VRBO
From $753 per night (USD)
Expedia
Luxury Waterfront Escape- Brand New Home In Venetian Shores
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to 104 Leoni Drive, a stunning new home in the highly sought-after Venetian Shores neighborhood of Islamorada. T ...
From $753 per night (USD)
Expedia
From $741 per night (USD)
VRBO
Maison 308 Seaside Cove
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to paradise at Maison Matecumbe in Islamorada! This beautiful 3-bedroom, 3-bathroom townhome offers an unforgett ...
From $741 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Pool Home in Venetian Shores
Bedrooms:
3
Bathrooms:
4
Sleeps:
16
Spacious, open layout designed for ultimate comfort and convenience. The fully equipped kitchen flows seamlessly into th ...
From $396 per night (USD)
Expedia
From $974 per night (USD)
VRBO
Nautica - Monthly 4 BR home on bay in Islamorada - Upper Matecumbe Key
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Mile Marker 83 – Bayfront Unfortunately all rentals must start on the 1st of the month. Island Villa Rentals and Owner' ...
From $974 per night (USD)
VRBO
From $146 per night (USD)
Expedia
Stunning Studio Apartment Summer Sea Condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Beautifully remodeled Studio with tropically décor, this 1st floor corner unit (steps required) has a private outdoor en ...
From $146 per night (USD)
Expedia
Click For Pricing
VRBO
Matecumbe Resort: Your Home Away From Home in the Florida Keys-1 Bedrm with View
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience Islamorada like a local in this superb 1-bedroom resort. The cozy bedroom features a king bed for a restful n ...
Click For Pricing
VRBO
From $304 per night (USD)
VRBO
Open Bay View Executive Bay Condo!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Professional photos coming soon! Step into your dream getaway! This beautifully renovated 2-bedroom, 2.5-bath townhome ...
From $304 per night (USD)
VRBO
From $501 per night (USD)
VRBO
Gorgeous, pool canal front home!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to your own slice of paradise in this stunning canal-front vacation home in Tavernier, Florida. This 3-bedroom, 2 ...
From $501 per night (USD)
VRBO
From $3276 per night (USD)
Expedia
Voted best boutique resort in Islamorada! Beach, dockage, pool + more!
Bedrooms:
8
Bathrooms:
8
Sleeps:
22
Located in the heart of Islamorada, Mermaid’s Bay Boutique Estate is a secluded oasis situated directly on the bay. Secu ...
From $3276 per night (USD)
Expedia
From $116 per night (USD)
VRBO
Charming 1 Bedroom Condo on Plantation Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Sit back and relax at Port o Palms. Experience the ultimate Florida Keys getaway at this light and bright one-bedroom, ...
From $116 per night (USD)
VRBO
From $2359 per night (USD)
Expedia
Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada
Bedrooms:
10
Bathrooms:
9
Sleeps:
18
Welcome to Infinity Bay Islamorada, an infinite paradise with infinite possibilities in the heart of the Florida Keys. T ...
From $2359 per night (USD)
Expedia
From $1866 per night (USD)
VRBO
Your Ultimate Keys Getaway Awaits!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Welcome to your dream getaway at Coastal Cove Villa! Nestled in the heart of downtown Islamorada, this spacious 4-bedroo ...
From $1866 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Newly Renovated - 2-bedroom state of the art condo Islamorada. Perfect Location!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Palms - Islamorada Brand New - Ripped down to the studs and just completed a $150k remodel with state of the art eve ...
From $339 per night (USD)
Expedia
From $287 per night (USD)
VRBO
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)
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
$The Sailfish House ~ 4 Bed \/ 4 Bath Luxury Oceanfront Home in Islamorada!$
From $1260 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 $1260 per night (USD)
VRBO
From $508 per night (USD)
Expedia
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)
Expedia
From $843 per night (USD)
VRBO
Spectacular Coastal Paradise with outstanding outdoor living spaces
Bedrooms:
7
Bathrooms:
5
Sleeps:
10
Escape to the islands in your own private resort. This Florida Keys home feels like your own private tropical oasis loc ...
From $843 per night (USD)
VRBO
From $372 per night (USD)
Expedia
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 $372 per night (USD)
Expedia
From $973 per night (USD)
VRBO
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 $973 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Charming Angler's Reef Home with Pool, Dock, Beach & Ocean View
Bedrooms:
3
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 $454 per night (USD)
Expedia
From $194 per night (USD)
VRBO
A 28 Day or More Rental
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 $194 per night (USD)
VRBO
From $447 per night (USD)
Expedia
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)
Expedia
From $3185 per night (USD)
VRBO
Private 150 Ft Oceanfront 2.5 Acre Estate with Saltwater Pool, Spa, Dock
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Completely renovated and expanded to over 3,700 square feet. San Roc is a private ocean front home with spectacular vie ...
From $3185 per night (USD)
VRBO
From $400 per night (USD)
Expedia
Best location 3BR house in Islamorada! Pool and beach; walk or bike everywhere.
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
AVAILABLE CHRISTMAS & NEW YEARS! Beautiful updated house on dead-end road with pool and private beach access. Launch a k ...
From $400 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
The "Nest" villa is one of only seven units nestled on a one acre native tropical hammock directly on Florida Bay with s ...
From $399 per night (USD)
VRBO
From $486 per night (USD)
Expedia
Light + Bright Islamorada Pool Home with Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Welcome to Islamorada Reef Home, a light and bright Islamorada pool home with dockage. You’ll feel right at home in th ...
From $486 per night (USD)
Expedia
From $516 per night (USD)
VRBO
Feel the breeze of the keys
Bedrooms:
4
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
Click For Pricing
Expedia
Pristine canal-front home with heated pool and access to open water
Bedrooms:
5
Bathrooms:
4
Sleeps:
9
Beautifully appointed getaway perfectly situated to allow exploration of the mangroves or the open water, since Tavernie ...
Click For Pricing
Expedia
$Canal-Front Florida Keys Home w\/ Dock!$
From $281 per night (USD)
VRBO
Canal-Front Florida Keys Home w\/ Dock!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Ocean breezes and beautiful water views are in store at this 2-bedroom, 2-bathroom home. This Florida Keys vacation rent ...
From $281 per night (USD)
VRBO
From $350 per night (USD)
Expedia
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $350 per night (USD)
Expedia
From $350 per night (USD)
VRBO
Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $350 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $280 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $280 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Ideal Location! Onsite Pool, Free Breakfast, Free Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $280 per night (USD)
Expedia
$Trendy canal-front home with dock, full kitchen, central AC, & washer\/dryer$
From $345 per night (USD)
VRBO
Trendy canal-front home with dock, full kitchen, central AC, & washer\/dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Salt House Swank Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $345 per night (USD)
VRBO
From $544 per night (USD)
Expedia
Enjoy the good life in the perfect Islamorada Home!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
133 Stromboli Drive - If ever you have imagined yourself vacationing in Islamorada, this home was in your head! Beautif ...
From $544 per night (USD)
Expedia
From $226 per night (USD)
VRBO
Reel Paradise at Sea Gulls
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Stunning ocean views and beautiful island sunrises! The Space: Welcome to Reel Paradise! This beautiful condo ...
From $226 per night (USD)
VRBO
From $603 per night (USD)
Expedia
Immaculate Islamorada Home with 100' of Dockage, Pool & More!
Bedrooms:
3
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)
Expedia
From $209 per night (USD)
VRBO
Zesty Lower Matecumbe Condo with Private Beach & Dockage
Bedrooms:
2
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 $209 per night (USD)
VRBO
$Bungalow #5 - 2 Bed\/1 Bath & Pool in Islamorada$
From $429 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 $429 per night (USD)
Expedia
From $222 per night (USD)
VRBO
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 $222 per night (USD)
VRBO
From $424 per night (USD)
VRBO
Sit back and relax in this beautiful Islamorada Pool home!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Put your mail on hold, your new Islamorada address is waiting! Sit back and relax in this beautiful Islamorada Pool ho ...
From $424 per night (USD)
VRBO
From $1074 per night (USD)
VRBO
The Villa by the Bay, Islamorada FL private plunge pool, boat dockage & sunsets
Bedrooms:
4
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 $1074 per night (USD)
VRBO
From $178 per night (USD)
Expedia
OCEAN FRONT TOWN HOUSE with breath taking views from all 3 balconies.
Bedrooms:
2
Bathrooms:
3
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)
Expedia
From $901 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 $901 per night (USD)
VRBO
From $438 per night (USD)
Expedia
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)
Expedia
From $448 per night (USD)
VRBO
Beautiful Keys Style Retreat - with bonus room, private pool and private dock.
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Experience paradise in our stunning 2-story, 2-bedroom, 3-bathroom rental property located in a peaceful residential nei ...
From $448 per night (USD)
VRBO
From $614 per night (USD)
Expedia
Venetian Shores 20K boat lift 28 day Minimum, ..August Cancellation now open....
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 $614 per night (USD)
Expedia
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
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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
Click For Pricing
VRBO
Comfy Townhome at Executive Bay Club - Marina, Pool, and Tennis!
Bedrooms:
3
Bathrooms:
2
Sleeps:
7
Enjoy this stylishly remodeled townhome in the Heart of Islamorada at Executive Bay Club. This 7-guest retreat features ...
Click For Pricing
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
$Luxury Home with 60' Deep Water Dock, Waterfall Pool, HotTub, A\/C and WiFi$
From $689 per night (USD)
VRBO
Luxury Home with 60' Deep Water Dock, Waterfall Pool, HotTub, A\/C and WiFi
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Minimum 28 day stay. Dreaming of a FL Keys vacation where you can boat, fish, dive, snorkel or stay home and swim in yo ...
From $689 per night (USD)
VRBO
From $775 per night (USD)
Expedia
Islamorada paradise vacation home in sought after Venation shores
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Location, location! Venetian Shores is the premier luxury private community with deep water access to Snake creek, which ...
From $775 per night (USD)
Expedia
From $381 per night (USD)
VRBO
Get ready to dive into your Islamorada Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
134 Tequesta Street - Get ready to dive into your Islamorada Winter Retreat! Move in ready today! This beautiful three-b ...
From $381 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Eclectic Easeful Stay At The Keys!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come and enjoy this spacious, airy, and recently renovated condo at Summer Sea in beautiful Tavernier, Florida. The buil ...
From $192 per night (USD)
Expedia
From $312 per night (USD)
VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $312 per night (USD)
VRBO
From $312 per night (USD)
Expedia
Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $312 per night (USD)
Expedia
From $437 per night (USD)
VRBO
ENDLESS SUMMER- Ocean side, private pool, pet friendly!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Pet friendly! Bring your boat and enjoy this large, 2-story house right on the ocean side. Private extra-large pool, Tik ...
From $437 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Escape to Paradise in Islamorada!
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Welcome to your perfect family-friendly getaway in the heart of Islamorada, Florida! Nestled between the sun-soaked shor ...
From $234 per night (USD)
Expedia

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