Islamorada Rentals
From $444 per night (USD)VRBO
Escape to Paradise! Beachfront, Outdoor Pool, Near Theater of the Sea
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to oceanfront tranquility at Islander Resort in Islamorada. Enjoy beach access, oceanfront pools, on-site dining, ...
From $444 per night (USD)VRBO
From $364 per night (USD)Expedia
Fun Under the Sun! Beachfront, w/ Pool Onsite, Free Parking, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $364 per night (USD)Expedia
From $1127 per night (USD)VRBO
You Don’t Want to Miss This! Beachfront, Onsite Pool, Near Coral Bay Marina
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $1127 per night (USD)VRBO
From $926 per night (USD)VRBO
Your Islamorada Hideaway! Beachfront Accommodation - Onsite Pool, Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $926 per night (USD)VRBO
From $1138 per night (USD)VRBO
Prime Location! Beachfront Property with Outdoor Pool, Pets are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $1138 per night (USD)VRBO
From $926 per night (USD)VRBO
Sun, Sand, and Relaxation Awaits! Ocean View Accommodation w/ Private Patio!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $926 per night (USD)VRBO
From $1326 per night (USD)VRBO
Family Getaway! 3 Tropical View Units, Outdoor Pools, Pet-friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located on a private beach and close to Indian Key Historic State Park. This listing is for 3 separate rooms within a h ...
From $1326 per night (USD)VRBO
From $922 per night (USD)VRBO
2 Spacious Units, Beachfront Property, Onsite Pool, Free Parking, Pet-friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located on a private beach and close to Indian Key Historic State Park. This listing is for 2 separate rooms within a h ...
From $922 per night (USD)VRBO
From $444 per night (USD)VRBO
Best Location! Beachfront Property with Outdoor Pool, Pets are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $444 per night (USD)VRBO
From $454 per night (USD)VRBO
Steps Away from Coral Bay Marina! Pool, Beachfront, Free Parking, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape to oceanfront tranquility at Islander Resort in Islamorada. Enjoy beach access, oceanfront pools, on-site dining, ...
From $454 per night (USD)VRBO
From $922 per night (USD)VRBO
Better Choice for your Vacation! 2 Comfortable Units, Beachfront, Outdoor Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located on a private beach and close to Indian Key Historic State Park. This listing is for 2 separate rooms within a h ...
From $922 per night (USD)VRBO
From $1326 per night (USD)VRBO
Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located on a private beach and close to Indian Key Historic State Park. This listing is for 3 separate rooms within a h ...
From $1326 per night (USD)VRBO
From $1256 per night (USD)VRBO
Enjoy a Hassle-free Stay! Unit w/ Full Kitchen, Beachfront, Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $1256 per night (USD)VRBO
From $1261 per night (USD)VRBO
Dip Your Toes In The Sand! Beachfront, Pool, Near History of Diving Museum
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $1261 per night (USD)VRBO
From $2103 per night (USD)VRBO
Keys to Relaxation! Pool, Pets Allowed, Short Drive to Florida Keys Airport
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $2103 per night (USD)VRBO
From $489 per night (USD)VRBO
Dream Paradise! Beachfront Property with Pool, Free Parking, Partial Ocean View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $489 per night (USD)VRBO
From $771 per night (USD)VRBO
Coastal Gem! Water Activities Onsite, Pool, Private Patio, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $771 per night (USD)VRBO
From $771 per night (USD)VRBO
Spacious Ocean View Accommodation w/ Patio! Beachfront Property w/ Outdoor Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $771 per night (USD)VRBO
From $757 per night (USD)VRBO
Excellent Choice! Beachfront Location, Outdoor Pool, Free Parking, Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $757 per night (USD)VRBO
From $1078 per night (USD)VRBO
Dive Into Your Dream Vacation! Beachfront, Outdoor Pool, Near Hurricane Monument
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $1078 per night (USD)VRBO
From $1135 per night (USD)VRBO
Beach Bliss, Just Steps to the Ocean! Outdoor Pool, Near Coral Bay Marina
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $1135 per night (USD)VRBO
From $549 per night (USD)VRBO
Summer Escapade! Onsite Pool, Steps from the Beach, Pets Allowed, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $549 per night (USD)VRBO
From $1078 per night (USD)VRBO
Best Vacation Choice! Outdoor Pool, Beachfront Location, Pets are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay close to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. Explore Indian Key Historic State Park and dive in ...
From $1078 per night (USD)VRBO
From $2108 per night (USD)VRBO
Have Fun at this Beachfront Paradise with Outdoor Pools, Free Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located on a private beach and close to Indian Key Historic State Park. This listing is for a room within a hotel. ✦ Y ...
From $2108 per night (USD)VRBO
From $466 per night (USD)VRBO
Ensuring a Very Comfortable & Memorable Stay, Near History of Diving Museum
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relaxing and indulgent stay on the tropical islands of Islamorada! ✦ Your room is 450 sq. ft, equipped with complimenta ...
From $466 per night (USD)VRBO
From $327 per night (USD)VRBO
Studio w/ King Bed, Kitchenette, Outdoor Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along a private beach in Islamorada, La Siesta Resort & Villas features studios with premium amenities. Guests enjoy ...
From $327 per night (USD)VRBO
From $385 per night (USD)VRBO
1 Bedroom Suite w/Kitchenette, Pool View, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $385 per night (USD)VRBO
From $396 per night (USD)VRBO
2 Bedroom Suite w/ Kitchenette, Outdoor Pool, Free Parking & Pet Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $396 per night (USD)VRBO
From $542 per night (USD)VRBO
Ocean Front Unit In Islamorada | Enjoy Scenic Walks on Private Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Set along a private beach in Islamorada, La Siesta Resort & Villas features colorful cottages with premium amenities. Gu ...
From $542 per night (USD)VRBO
From $720 per night (USD)VRBO
Two Spacious 1BR Suites w/ Scenic Pool View | Breathtaking Resort | Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $720 per night (USD)VRBO
From $1073 per night (USD)VRBO
Scenic Beachfront Suite w/ Gorgeous Views & Family-Friendly Pool | Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This listing is for a room within a hotel. ✦ Your room is 850 sq. ft, equipped with complimentary toiletries, TV. ✦ Da ...
From $1073 per night (USD)VRBO
From $975 per night (USD)VRBO
2 Bedroom Suite in Islamorada! Swimming Pool, Kitchenette, Pets Allowed!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront suites with premium amenities. Gu ...
From $975 per night (USD)VRBO
From $314 per night (USD)VRBO
Studio w/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Set along a private beach in Islamorada, La Siesta Resort & Villas features studios with premium amenities. Guests enjoy ...
From $314 per night (USD)VRBO
From $423 per night (USD)VRBO
A Place You'll Surely Enjoy! Courtyard View, Free Parking, Onsite Pool
- 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 $423 per night (USD)VRBO
From $324 per night (USD)VRBO
Spacious 1BR Suite w/Kitchenette, Outdoor Pool, Free Parking & Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Set along a private beach in Islamorada, La Siesta Resort & Villas features suites with premium amenities. Guests enjoy ...
From $324 per night (USD)VRBO
From $423 per night (USD)VRBO
Relax and Unwind! Courtyard View, Free Parking, Onsite Pool, 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 $423 per night (USD)VRBO
From $629 per night (USD)VRBO
Newly built 4-bedroom house in Tavernier with ample dock space and Kayak ramp.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This Tavernier house boasts 4 inviting bedrooms - 2 king beds, 2 queen beds, and 1 bunk bed. With 3 bathrooms featuring ...
From $629 per night (USD)VRBO
From $404 per night (USD)VRBO
Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property
- 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 $404 per night (USD)VRBO
From $867 per night (USD)VRBO
Relax and Recharge in Islamorada! 2 Relaxing Units, Pets Allowed, Outdoor 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 $867 per night (USD)VRBO
From $1035 per night (USD)VRBO
Relax and Unwind in Islamorada! Swimming Pool, Pet-friendly Property!
- 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 $1035 per night (USD)VRBO
From $1620 per night (USD)VRBO
A Place You'll Surely Enjoy! 3 Comfortable Units, Onsite Pool, Free Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $1620 per night (USD)VRBO
From $1082 per night (USD)VRBO
High Tides and Good Vibes! 2 Relaxing Units, Pet-friendly Property, 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 $1082 per night (USD)VRBO
From $2166 per night (USD)VRBO
Make Your Trip More Enjoyable! 4 Family-friendly Units, Pets Allowed, Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $2166 per night (USD)VRBO
From $441 per night (USD)VRBO
Best Place to Unwind! Free Parking, Pet-friendly Property, 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 $441 per night (USD)VRBO
From $450 per night (USD)VRBO
2 Queen Beds Room w/ Balcony, Outdoor Pool, Free Parking & Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island ...
From $450 per night (USD)VRBO
From $441 per night (USD)VRBO
Comfort and Relaxation! Free Parking, Minutes to History of Diving Museum
- 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 $441 per night (USD)VRBO
From $417 per night (USD)VRBO
Enjoy a Hassle-Free Stay! Free Parking, Onsite Pool, 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 $417 per night (USD)VRBO
From $404 per night (USD)VRBO
Best Place to Unwind! Free Parking, Onsite Pool, Short Drive to Anne's 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 $404 per night (USD)VRBO
From $541 per night (USD)VRBO
Home Away from Home in Islamorada! Pets Allowed, Free Parking, Outdoor 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 $541 per night (USD)VRBO
From $1624 per night (USD)VRBO
Short Distance From The Well Known Sites! 3 Family-friendly Units, Free Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $1624 per night (USD)VRBO
From $290 per night (USD)VRBO
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)VRBO
From $241 per night (USD)Expedia
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 $241 per night (USD)Expedia
From $305 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 $305 per night (USD)VRBO
From $295 per night (USD)Expedia
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)Expedia
From $688 per night (USD)VRBO
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 $688 per night (USD)VRBO
From $316 per night (USD)Expedia
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 $316 per night (USD)Expedia
From $588 per night (USD)VRBO
Peaceful Retreat in Islamorada! Pet-friendly, Swimming Pool, 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 $588 per night (USD)VRBO
From $460 per night (USD)VRBO
Indulge in Home Like Comfort! Courtyard View, Free Parking, 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 $460 per night (USD)VRBO
From $311 per night (USD)VRBO
Cozy waterfront home with dock, BBQ, dog friendly, AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Treasure Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $311 per night (USD)VRBO
From $393 per night (USD)Expedia
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 ...
From $393 per night (USD)Expedia
From $319 per night (USD)VRBO
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)VRBO
From $3453 per night (USD)VRBO
PRIVATE BEACH, Pickleball Court and Tiki Bar/ 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 $3453 per night (USD)VRBO
From $541 per night (USD)VRBO
Relaxation at Its Finest in Islamorada! Free Parking, 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 $541 per night (USD)VRBO
From $2166 per night (USD)VRBO
Indulge in Home Like Comfort! 4 Pleasant Units, Free Parking, Onsite Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive in ...
From $2166 per night (USD)VRBO
From $418 per night (USD)VRBO
Always a Great Idea To Unwind! Free Parking, Onsite Pool, Pet-friendly
- 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 $418 per night (USD)VRBO
From $821 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 $821 per night (USD)VRBO
From $819 per night (USD)VRBO
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 $819 per night (USD)VRBO
From $1035 per night (USD)VRBO
Your Dream Escape in Islamorada! Pet-friendly Property, Swimming Pool!
- 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 $1035 per night (USD)VRBO
From $562 per night (USD)VRBO
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 $562 per night (USD)VRBO
From $1082 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 $1082 per night (USD)VRBO
From $624 per night (USD)VRBO
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 $624 per night (USD)VRBO
From $433 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 $433 per night (USD)VRBO
From $474 per night (USD)VRBO
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 $474 per night (USD)VRBO
From $867 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 $867 per night (USD)VRBO
From $475 per night (USD)VRBO
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 $475 per night (USD)VRBO
From $525 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 $525 per night (USD)VRBO
From $771 per night (USD)VRBO
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 $771 per night (USD)VRBO
From $476 per night (USD)VRBO
Better Choice For Your Vacation, Near History of Diving Museum, Pets are Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relaxing and indulgent stay on the tropical islands of Islamorada! ✦ Your room is 450 sq. ft, equipped with complimenta ...
From $476 per night (USD)VRBO
From $1141 per night (USD)VRBO
Best Value, Quality Stay with Free Parking, Near Islamorada Brewery & Distillery
- 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 $1141 per night (USD)VRBO
From $476 per night (USD)VRBO
Sunny Escape! Spacious Oceanfront Suite with Balcony! Beachfront Resort w/ Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $476 per night (USD)VRBO
From $715 per night (USD)VRBO
Your Key to Unforgettable Island Moments! 2 Relaxing Units with Balcony!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Aloha! Located off the Overseas Highway in Islamorada, swim with dolphins or visit Sea Oats Beach all within easy reach. ...
From $715 per night (USD)VRBO
From $900 per night (USD)VRBO
Relaxation at its Finest in Islamorada! Swimming Pool, Beach, Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Relaxing and indulgent stay on the tropical islands of Islamorada! This listing is for a room within a hotel. ✦ Your r ...
From $900 per night (USD)VRBO
From $500 per night (USD)VRBO
Ideal Mix of Comfort & Value! Studio 2 Queen beds w/ Pool & Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios with premium amenities. G ...
From $500 per night (USD)VRBO
From $648 per night (USD)VRBO
2 Spacious Garden Suite w/ Kitchenette | Outdoor Pool + Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $648 per night (USD)VRBO
From $569 per night (USD)VRBO
Relax, Play, and Soak in Islamorada! Swimming Pool, Pets Allowed, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relaxing and indulgent stay on the tropical islands of Islamorada! ✦ Your room is 450 sq. ft, equipped with complimenta ...
From $569 per night (USD)VRBO
From $686 per night (USD)VRBO
Peaceful Mornings in Islamorada! Swimming Pool, Beach, Pet-friendly!
- 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 $686 per night (USD)VRBO
From $444 per night (USD)VRBO
Indulge in Home Like Comfort! Free Parking, Onsite Pool, Pet-friendly Property
- 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 $444 per night (USD)VRBO
From $772 per night (USD)VRBO
Waterfront Elegance in Islamorada! Beach, Swimming Pool, Pet-friendly!
- 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 $772 per night (USD)VRBO
From $514 per night (USD)VRBO
Ideal Mix of Comfort and Value! Pool, Free Parking, Near Anne's Beach & Sea Oats
- 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 $514 per night (USD)VRBO
From $510 per night (USD)VRBO
Indulge in Home-Like Comfort! Free Parking, Pool, Pet-friendly Property
- 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 $510 per night (USD)VRBO
From $460 per night (USD)VRBO
Make Your Trip More Enjoyable! Free Parking, Pets Allowed, 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 $460 per night (USD)VRBO
From $456 per night (USD)VRBO
Embrace the Sugar Rush Experience! Courtyard View, Free Parking, Onsite Pool
- 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 $456 per night (USD)VRBO
From $495 per night (USD)VRBO
Spacious Good-Value Accommodation! Free Parking, Onsite 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 $495 per night (USD)VRBO
From $484 per night (USD)VRBO
Indulge in Home Like Comfort! Free Parking, Onsite 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 $484 per night (USD)VRBO
From $525 per night (USD)VRBO
Your Charming Stay in Islamorada! Beach, Swimming Pool, Pets Allowed!
- 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 $525 per night (USD)VRBO
From $908 per night (USD)Expedia
Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish c ...
From $908 per night (USD)Expedia
From $1401 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 $1401 per night (USD)VRBO
From $733 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 $733 per night (USD)Expedia
Click For PricingVRBO
Come relax in this oceanside 2 bedroom home, in a pet friendly resort!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This home has amazing views of the Atlantic, and has 2 two bedroom, two baths. The vibe is tasteful and relaxing - jus ...
Click For PricingVRBO
From $235 per night (USD)Expedia
Charming 2-bedroom home in brilliant Tavernier near Marinas and Founders Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind in Tavernier at this delightful home. This charming property features 2 bedrooms - one with a king bed and the ot ...
From $235 per night (USD)Expedia