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

Islamorada Rentals

From $353 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 $353 per night (USD)
VRBO
From $640 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 $640 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 $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 $277 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 $277 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 $583 per night (USD)
VRBO
30’+ of dock available oceanside
Bedrooms:
4
Bathrooms:
6
Sleeps:
8
Walking distance of grocery stores, 4000+ square feet of living space! Located at 90 mile marker in Islamorada. Lots o ...
From $583 per night (USD)
VRBO
From $216 per night (USD)
Expedia
Sandy Toes Await At This Beach Front Sandy Point Condo!
Bedrooms:
2
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)
Expedia
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 $509 per night (USD)
Expedia
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)
Expedia
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 $308 per night (USD)
Expedia
NEW HOME and BOAT SLIP, pet friendly all in a resort!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This brand new home is sitting quietly behind a controlled access gate with a personal view of the Atlantic Ocean and ha ...
From $308 per night (USD)
Expedia
$Waterfront w\/boat slip, New Construction$
From $308 per night (USD)
VRBO
Waterfront w\/boat slip, New Construction
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Prime location for a relaxing stay, take in the views of the Atlantic from your private balcony. Two bedroom, two bath, ...
From $308 per night (USD)
VRBO
From $297 per night (USD)
Expedia
New Home, Waterfront, Boat Slip Included
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Brand new resort offering first class amenities, in the heart of Islamorada, near many restaurants, and across the stree ...
From $297 per night (USD)
Expedia
From $273 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 $273 per night (USD)
VRBO
From $473 per night (USD)
Expedia
Gorgeous Keys Vacation Home in Prestigious Neighborhood of Port Antigua
Bedrooms:
3
Bathrooms:
6
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 $315 per night (USD)
VRBO
FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full baths
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full bathrooms and a loft for gaming etc. freshly ...
From $315 per night (USD)
VRBO
$Keys home on water w\/ access to beach *monthly*$
Click For Pricing
Expedia
Keys home on water w\/ access to beach *monthly*
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Canal front house in the white marlin beach neighborhood of Lower Matecumbe (Islamorada) The space Three bedroom two bat ...
Click For Pricing
Expedia
$Three Villa w\/ Living Area & Private Patio | Close to Theater of the Sea$
From $1635 per night (USD)
VRBO
Three Villa w\/ Living Area & Private Patio | Close to Theater of the Sea
Bedrooms:
6
Bathrooms:
6
Sleeps:
18
Discover your home away from home in the Florida Keys. Come enjoy pristine beaches, heart-racing water sports, and stunn ...
From $1635 per night (USD)
VRBO
From $460 per night (USD)
Expedia
Spacious 5-bedroom house with AC and WiFi in welcoming Tavernier
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Enjoy a peaceful stay at this 5-bedroom house in Tavernier. This superb property offers a beautiful blend of comfort and ...
From $460 per night (USD)
Expedia
From $223 per night (USD)
VRBO
Cozy Oceanfront Studio in the Heart of Islamorada.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This property sits directly behind the main oceanfront house on the same property, Your Islamorada adventure begins at t ...
From $223 per night (USD)
VRBO
From $353 per night (USD)
Expedia
Manatee Manor ~ 3 Bedroom Island Home on Plantation Key with Pool & Dockage
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Swim. Sleep. Repeat., at Manatee Manor. This 3-bedroom, 2.5-bath home on Plantation Key has something for everyone. Enjo ...
From $353 per night (USD)
Expedia
From $194 per night (USD)
VRBO
Tropical Oasis Anchor located on the bay side. Community private boat ramp.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Tropical Oasis Anchor a Beautiful Place To Stay conveniently located just two blocks away from private community boat r ...
From $194 per night (USD)
VRBO
Click For Pricing
Expedia
THIS is the ONE!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Perfect for the whole family! Enjoy this spacious and newly remodeled unit in a private community. Beach and pool access ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Luxury One Bedroom Condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One Bedroom, One Bathroom Condo, Separate Living Space and Fully Equipped Kitchen. Outdoor Fire pit under palm trees w ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Luxury One Bedroom Condo #3
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
One Bedroom, One Bathroom Condo, Separate Living Space and Fully Equipped Kitchen. Outdoor Fire pit under palm trees w ...
Click For Pricing
Expedia
$Create Memories w\/ Fun-filled Adventures at this P$
From $1162 per night (USD)
VRBO
Create Memories w\/ Fun-filled Adventures at this P
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $1162 per night (USD)
VRBO
From $632 per night (USD)
Expedia
Modern ground-floor apartment with pool, water views, patio, grill, & central AC
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Treasure Harbor Hideaway - Lower Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $632 per night (USD)
Expedia
From $649 per night (USD)
VRBO
Deluxe upper apartment with pool, canal-view balcony, water access, grill, & AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Treasure Harbor Hideaway - Upper Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $649 per night (USD)
VRBO
From $429 per night (USD)
Expedia
Your Blissful Haven in Islamorada! Beach, Swimming Pool, Pets Allowed!
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 $429 per night (USD)
Expedia
From $387 per night (USD)
VRBO
Indulge in Home Like Comfort! Oceanfront, Free Parking, 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 $387 per night (USD)
VRBO
From $421 per night (USD)
Expedia
Fun and Sun in Islamorada! Free Parking, Swimming 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 $421 per night (USD)
Expedia
From $393 per night (USD)
VRBO
Enjoy a Hassle-Free and Suiting Stay! Pets Allowed, 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 $393 per night (USD)
VRBO
From $251 per night (USD)
Expedia
Captains Quarters is a charming canal front Keys house in delightful Islamorada
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your cozy getaway awaits in Islamorada at this superb house. With 2 bedrooms including 1 king, 1 queen, and 2 twin beds ...
From $251 per night (USD)
Expedia
From $340 per night (USD)
VRBO
Matecumbe Resort: 2 Bedroom Oceanview. Your Home Away From Home in the FL Keys.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Matecumbe Resort offers well-appointed, air-conditioned accommodations in Islamorada, renowned as the fishing capital of ...
From $340 per night (USD)
VRBO
$Winterbirds! Charming studio in the Port Antigua Islamorada Florida Keys\n$
From $148 per night (USD)
Expedia
Winterbirds! Charming studio in the Port Antigua Islamorada Florida Keys\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome winter birds to this enchanting studio in Islamorada Florida Keys. This cozy retreat offers TV, AC, WiFi, kitche ...
From $148 per night (USD)
Expedia
From $1110 per night (USD)
VRBO
Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Located in Islamorada, enjoy what this 3-bedroom villa has to offer. With 2 king beds and 1 queen bed, guests can relax ...
From $1110 per night (USD)
VRBO
From $490 per night (USD)
Expedia
Luxury 2BR Waterfront Futura Condo
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Discover paradise in this 2-bedroom, 2.5-bath townhouse in the heart of the Florida Keys. Enjoy a private marina 10 feet ...
From $490 per night (USD)
Expedia
From $270 per night (USD)
VRBO
Brand New! 2-bedroom house in Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This brand new home is sitting quietly behind a controlled access gate with a personal view of the Atlantic Ocean. Full ...
From $270 per night (USD)
VRBO
From $459 per night (USD)
Expedia
Beautiful ocean front private beach 2-bedroom house gorgeous views Isla morada
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in Islamorada, this peaceful 2-bedroom house. Ocean front -Private beach is a welcoming retreat for guests. this ...
From $459 per night (USD)
Expedia
From $219 per night (USD)
VRBO
Updated 3-bedroom Townhome at Executive Bay Club resort
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This spacious, fully remodeled 3-bedroom, 2-bathroom loft townhome is located in the heart of Islamorada at the exclusiv ...
From $219 per night (USD)
VRBO
From $238 per night (USD)
Expedia
3-bedroom Townhome with Direct Ocean Views at resort in Islamorada
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape to paradise in this gorgeous 3-bedroom, 3-bathroom townhome is located at Executive Bay Club in Islamorada, FL. I ...
From $238 per night (USD)
Expedia
Click For Pricing
VRBO
3-bedroom condo in charming Tavernier with AC, WiFi. Relax and unwind
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to this charming condo in Tavernier. This delightful property features 3 cozy bedrooms with a mix of a king bed, ...
Click For Pricing
VRBO
From $1457 per night (USD)
Expedia
Luxury Oceanfront Estate in Islamorada - Your Tropical Paradise Awaits!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Welcome to Orchid Beach, your ultimate oceanside escape! Nestled directly on the beach, this gated estate greets you wit ...
From $1457 per night (USD)
Expedia
From $610 per night (USD)
VRBO
Islamorada Cay ~ Resort Style 4 Bed Plantation Key Home with Pool & 100' Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Chill out in style at Islamorada Cay! This resort style, 4-bedroom, 3-bathroom canal-front property is nestled in the id ...
From $610 per night (USD)
VRBO
$Bayside Home Dock\/Lift quick to ocean perfect spot to enjoy the best of the Keys$
From $295 per night (USD)
Expedia
Bayside Home Dock\/Lift quick to ocean perfect spot to enjoy the best of the Keys
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Waterfront home with dock & lift (6k dry weight max) small ramp for your kayaks & paddle boards has direct access to bay ...
From $295 per night (USD)
Expedia
$Peninsula Villa \/ Heated Pool \/ Sunset Point$
From $3335 per night (USD)
VRBO
Peninsula Villa \/ Heated Pool \/ Sunset Point
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
This grand peninsula retreat is embraced by the Ocean and lush mangroves, offering privacy to the heated pool with its t ...
From $3335 per night (USD)
VRBO
From $633 per night (USD)
Expedia
Southern Comfort - Charming oceanfront private oasis!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Welcome to Southern Comfort, your home away from home! Your ideal oceanfront getaway boasting 3 bedrooms and 4 baths an ...
From $633 per night (USD)
Expedia
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 $279 per night (USD)
Expedia
Classic canal home with vintage charm!
Bedrooms:
2
Bathrooms:
4
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)
Expedia
From $555 per night (USD)
VRBO
Island Oasis in Islamorada: Your Private Paradise Awaits!
Bedrooms:
3
Bathrooms:
4
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 $684 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 $684 per night (USD)
Expedia
From $287 per night (USD)
VRBO
Waterfront property with a pool and great spot for fishing Islamorada FL
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Follow your dream vacation keys home to 124 Gardenia St.. A water direct view offering an open dock and a pool area. The ...
From $287 per night (USD)
VRBO
$Islamorada Key Waterfront House w\/ Private Boat Dock$
From $404 per night (USD)
Expedia
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 $404 per night (USD)
Expedia
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 $353 per night (USD)
Expedia
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 $353 per night (USD)
Expedia
From $1691 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 $1691 per night (USD)
VRBO
From $462 per night (USD)
Expedia
Cozy Islamorada retreat!
Bedrooms:
3
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)
Expedia
From $425 per night (USD)
VRBO
Fabulous Futura Yacht Club Townhome with boat slip!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Your own tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada. Futura Yacht Club is a 70 unit c ...
From $425 per night (USD)
VRBO
From $424 per night (USD)
Expedia
Oceanfront, Private Pool Oasis!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Indulge in a retreat to paradise at this exquisite 3-bedroom, 3-bathroom oceanfront home on the captivating shores of Is ...
From $424 per night (USD)
Expedia
From $2273 per night (USD)
VRBO
Blue Ocean Estate, 3 bedroom ocean front in Islamorada, rented by Island Villa
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Mile Marker 81 - Oceanfront Welcome to your exclusive oceanfront oasis in Islamorada, in the Florida Keys! This 3-bedro ...
From $2273 per night (USD)
VRBO
From $278 per night (USD)
Expedia
Updated Canal Front Home in Indian Waterways
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Perfectly located and fully updated waterfront home with a private dock. Bring your boat and you’re five minutes from th ...
From $278 per night (USD)
Expedia
From $637 per night (USD)
VRBO
Breathtaking Ocean Views At This Penthouse Suite!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our penthouse condo, a stunning vacation rental with breathtaking ocean views. This modern and tastefully fur ...
From $637 per night (USD)
VRBO
$5 Bedroom \/ 4 Bath Relaxed Plantation Key Resort Style Home with Pool & Dockage$
From $564 per night (USD)
Expedia
5 Bedroom \/ 4 Bath Relaxed Plantation Key Resort Style Home with Pool & Dockage
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Greetings from Captain's Quarters! Located on Plantation Key (Mile Marker 90), this beautifully updated five bedroom and ...
From $564 per night (USD)
Expedia
From $351 per night (USD)
VRBO
Caribbean style home Islamorada - Oceanfront resort privileges.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Indulge in the allure of the Florida Keys with our Caribbean retreat nestled in the heart of Islamorada. Immerse yoursel ...
From $351 per night (USD)
VRBO
From $296 per night (USD)
Expedia
Coastal Island Retreat with Private Beach Access!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Time Well Wasted, an ideal retreat located in the highly sought-after neighborhood of Port Antiqua on Lower M ...
From $296 per night (USD)
Expedia
From $1173 per night (USD)
VRBO
Beautiful bayfront house, private pool and dock, right in Downtown Islamorada
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Relaxing is made easy at Coral Cove 8, moving from open, airy living spaces to your own private pool. Bright modern fin ...
From $1173 per night (USD)
VRBO
From $1154 per night (USD)
Expedia
Brand New 4-Bedroom Oceanfront Home in the Heart of Islamorada
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Immerse yourself in the luxury and beauty of Oceanside Resort, a brand-new gated community with 9 beachfront homes nestl ...
From $1154 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Cute Canal Front Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Two Bedroom one bath, one sleeper sofa canal front cottage. Enjoy the 50 foot dock on a deep water canal. Fully equippe ...
From $169 per night (USD)
VRBO
From $510 per night (USD)
Expedia
Mojito Breeze Getaway
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
Beachy but elegant, close to mainland FL, sleeps 12 comfortably, timeless tropical getaway, plenty of room Nice, quiet ...
From $510 per night (USD)
Expedia
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 $184 per night (USD)
Expedia
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)
Expedia
From $397 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 $397 per night (USD)
VRBO
From $1153 per night (USD)
Expedia
Jamaican Palm House 3 Bedrooms, 2 Bath, Poolside
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Poolside,3 Queen Beds,1 Pull Out Welcome to the Jamaican Palm. Our most recently renovated home is a sight to behold. E ...
From $1153 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Ocean Side Condo In Paradise Mm 76.5-Islamorada, Fl (28 day minimum required)
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
This is a quaint, ocean side condo with full amenities and easy access for fishing, diving, snorkeling and much more.The ...
From $203 per night (USD)
VRBO
$Spectacular Penthouse w\/Panoramic Open Water Views-New rental$
From $236 per night (USD)
Expedia
Spectacular Penthouse w\/Panoramic Open Water Views-New rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Fantastic Penthouse Apartment is just steps away from the fabulous turquoise waters of Florida Bay! Enjoy spectacul ...
From $236 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Just What You Were Looking For! Free Breakfast, Onsite Pool, 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 $304 per night (USD)
VRBO
From $765 per night (USD)
Expedia
Canary Island Palm South 2 Bedrooms, 2 Baths, Poolside
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Poolside,1 King Bed, 2 Queen Beds, 1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. Rich mahog ...
From $765 per night (USD)
Expedia
From $567 per night (USD)
VRBO
Fish Tail Palm Ocean View 1 Queen Bed, and 1 Pull Out
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Ocean View 1 Queen Bed, and 1 Pull Out. Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, ...
From $567 per night (USD)
VRBO
From $774 per night (USD)
Expedia
Canary Island Palm North Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoga ...
From $774 per night (USD)
Expedia
From $768 per night (USD)
VRBO
Coconut Palm South,1 King Bed, 2 Full Beds, 1 Pull Out
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
1 King Bed, 2 Full Beds, 1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, tea ...
From $768 per night (USD)
VRBO
From $788 per night (USD)
Expedia
Harbor house 2 Bedrooms, 2 Baths, Partial Ocean View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Partial Ocean View 1 King Bed, 1 Queen Bed, 1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. R ...
From $788 per night (USD)
Expedia
From $679 per night (USD)
VRBO
Island Time - Plantation Key Home with 4 beds & 3 baths with Pool & Dockage
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Island Time! This newly constructed canal front residence located in the heart of Plantation Key is sure to ...
From $679 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Beautiful, Spacious, Single Story Home - Islamorada
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This single-story canal front home located in the heart of Islamorada (MM86) in the Florida Keys-fishing capital of the ...
From $342 per night (USD)
Expedia
$TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE\/VIEW COMPLETELY REMODELED$
From $404 per night (USD)
VRBO
TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE\/VIEW COMPLETELY REMODELED
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
New In Ground Heated pool , Just remodeled with new furniture, flat screen tvs throughout ( including the patio) and a d ...
From $404 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Beautiful Venetian Shores canal home with dockage!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
130 Stromboli Drive - Beautiful Venetian Shores canal home that has two-bedroom two bath upstairs and a one-bedroom one ...
From $402 per night (USD)
Expedia
From $47073 per night (USD)
VRBO
Ultra-Luxury Exclusive Private Oceanfront Estate - White Glove Service Available
Bedrooms:
10
Bathrooms:
7
Sleeps:
14
* Exquisite White Glove Service is Available for an additional fee. See below. We proudly present the first of its col ...
From $47073 per night (USD)
VRBO
$Open February 2024! \Paradise South\ ~ Chic Island Home with Pool & Dockage$
From $567 per night (USD)
Expedia
Open February 2024! \"Paradise South\" ~ Chic Island Home with Pool & Dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Paradise South! This delightful 3 bedroom, 2 bath home in the heart of Plantation Key welcomes you for your ...
From $567 per night (USD)
Expedia
From $173 per night (USD)
VRBO
Home in Paradise- Islamorada Cottage,p Pool & Dockage
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Totally remodeled, canal front home, quiet and in the nicest neighborhoods (Plantation Key Colony). Situated on the bays ...
From $173 per night (USD)
VRBO
$Impressive Resort Like 5 Bedroom \/ 4.5 Baths with Pool & Dockage in Islamorada!$
From $606 per night (USD)
Expedia
Impressive Resort Like 5 Bedroom \/ 4.5 Baths with Pool & Dockage in Islamorada!
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Located on a cul-de-sac in the charming city of Islamorada, this beautifully- appointed five-bedroom, four and a half-ba ...
From $606 per night (USD)
Expedia
$ULTIMATE outdoor living area at this 4\/4 canal home with pool!$
From $624 per night (USD)
VRBO
ULTIMATE outdoor living area at this 4\/4 canal home with pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This beautifully remodeled home in desirable Plantation Key Colony has the sought-after amenities of a large resort, in ...
From $624 per night (USD)
VRBO
$Keys Waterfront House with large pool 30' Dock w\/ 50 Amp power 10% off Nov-Feb$
From $450 per night (USD)
Expedia
Keys Waterfront House with large pool 30' Dock w\/ 50 Amp power 10% off Nov-Feb
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
NOW OFFERING A SPECIAL RATE OF 10% OFF FOR BOOKINGS FROM DECEMBER 2024 THROUGH FEBUARY 2025 ONLY, Fishermans parad ...
From $450 per night (USD)
Expedia
From $1122 per night (USD)
VRBO
Tropical retreat where location meets quintessential Keys vacation home.
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Heart of Morada - This unique townhome is located bay front at Mile Marker 81.5 on U.S. Highway 1 in the heart of downto ...
From $1122 per night (USD)
VRBO
From $413 per night (USD)
Expedia
Futura Yacht Club Bayfront Townhome with Endless Sunsets!
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
Endless Sunsets!! This is a beautiful Bayfront Townhome in Islamorada's popular Futura Yacht Club. 3 level townhome w ...
From $413 per night (USD)
Expedia
$Venetian Shores Home -DOCK remodeled 3\/3 POOL\/Hot Tub! Deep water Dockage$
From $518 per night (USD)
VRBO
Venetian Shores Home -DOCK remodeled 3\/3 POOL\/Hot Tub! Deep water Dockage
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
126 Palermo Drive Check out this new to the Vacation Rental Market home in Venetian Shores on canal with 70' dock, pool, ...
From $518 per night (USD)
VRBO
From $264 per night (USD)
Expedia
Best Location for Your best vacation!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Best Home to Share with Family and Friends! This Beautiful Home consists of 2 levels with 2 separate units. The 1st leve ...
From $264 per night (USD)
Expedia
From $492 per night (USD)
VRBO
New saltwater pool, pet friendly, waterfront house with dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,0 ...
From $492 per night (USD)
VRBO
$Updated 3\/2 condo Futura Yacht Club-Spacious Open Floor Plan, Sunset VIEWS!$
From $465 per night (USD)
Expedia
Updated 3\/2 condo Futura Yacht Club-Spacious Open Floor Plan, Sunset VIEWS!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Gorgeous completely remodeled spacious condo in the highly sought after Futura Yacht Club overlooking Florida Bay with s ...
From $465 per night (USD)
Expedia
From $496 per night (USD)
VRBO
Beautiful New Pool Home located in a gated community in the Heart of Islamorada.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
29 Flamingo Hammock Road - This Beautiful Ground-Level Vacation Retreat awaits your arrival. Walk into this home and you ...
From $496 per night (USD)
VRBO
From $542 per night (USD)
Expedia
NEW Luxury Modern Coastal Home in Islamorada
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This New construction has all the bells and whistles to make your stay unforgettable. Located in the heart of Islamorada ...
From $542 per night (USD)
Expedia

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