Find short term rentals in Islamorada, FL at the best prices
971 available short term rental offers
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Best Short term and Weekly rentals in Islamorada, FL
9.8 29 reviews
Islamorada, FL
01/07 – 08/07
$712/nighttotal: $4984 (7 )
3/2 Condo Futura Yacht Club Pool, Dockage, Wifi, Dockage, Beach
3 2
apartment , Islamorada, Village of Islands
This waterfront condominium in Tavernier, located 108 kilometres south of Miami, offers prime access within the gated Futura Yacht Club community, close to Indian Key Historic State Park and the Hurricane Monument. This family-friendly, 118 square metre apartment boasts three bedrooms and two bathrooms, accommodating up to six guests with a private balcony, swimming pool, tennis courts, and a boat dockage for vessels up to 36 feet.
9.8 27 reviews
Islamorada, FL
17/10 – 26/10
$637/nighttotal: $5733 (9 )
Islamorada Luxury Waterfront Condo With Boat Slip
2 6
apartment , Islamorada, Village of Islands
This two-bedroom apartment is located in the Matecumbe district of Islamorada, just a short distance from mile marker 75, offering easy access to fishing, diving, and other water activities. It has been rated excellent by previous guests. The apartment is 139 square metres in size and comfortably sleeps up to 6 guests. It features a fully equipped kitchen, two master bedrooms with private bathrooms, a private boat slip, a heated swimming pool, a hot tub, a clubhouse, a fitness centre, tennis courts, gas barbeque grills, tennis equipment, beach chairs, and coolers.
10 15 reviews
Islamorada, FL
22/06 – 02/07
$499/nighttotal: $4990 (10 )
Gulf View Retreat @ Bay Harbor
2 2
apartment , Islamorada, Village of Islands
This two-bedroom apartment is situated in Matecumbe, just 3.5 kilometres from Sunset Drive Beach and Anne's Beach, and 3.5 kilometres from San Pedro Underwater Archaeological Preserve State Park. This highly rated property offers a comfortable and convenient stay for travellers seeking a relaxing getaway in the Florida Keys. The apartment can accommodate up to four guests and features a fully equipped kitchen, a washing machine, a terrace, a garden, a swimming pool, a jacuzzi and a fitness centre. Guests can enjoy a range of amenities and activities, including relaxing by the pool, exploring the nearby beaches, and enjoying the beautiful surroundings.
10 121 reviews
Islamorada, FL
17/10 – 26/10
$859/nighttotal: $7731 (9 )
4 Bedroom House In Angler's Reef, Includes 31' Boat Slip. Islamorada, Fl
4 6
apartment , Islamorada, Village of Islands
This boat is located in Angler's Reef, a gated community in Islamorada, offering direct beach access and close proximity to the Florida Keys Brewing Co. and Florida Keys Dive Center. The property boasts excellent user ratings and is perfect for families and pet owners. The boat is spacious, offering 184 square meters of living space with four bedrooms and four bathrooms, comfortably accommodating up to eight guests. Enjoy a fully equipped kitchen, a private boat slip, a swimming pool, a jacuzzi, and direct access to the beach, making it an ideal choice for a relaxing and enjoyable stay in the Florida Keys.
Islamorada, FL
03/07 – 05/07
$799/nighttotal: $1598 (2 )
Ocean View 2br Condo Pool, Beach, Near The Fun
2 5
apartment , Tavernier
This Tavernier oceanfront apartment offers direct beach access and is situated near John Pennekamp Coral Reef State Park and Indian Key Historic State Park, with proximity to attractions such as the Old Road Gallery and History of Diving Museum. The 79 square metre self-catering property features two bedrooms (one with a king or queen bed, the other with twin or queen beds) plus a sofa bed, accommodating up to six guests, and includes a kitchen with fridge, microwave, and dishwasher, air conditioning, a swimming pool, parking, and internet access.
9.7 41 reviews
Islamorada, FL
01/07 – 08/07
$678/nighttotal: $4746 (7 )
Anglers Reef Is Oceanfront, Blue Marlin House2/2.5
2 2
apartment , Islamorada, Village of Islands
The Blue Marlin house, a Key West-style property in Islamorada's Anglers Reef neighbourhood, is situated approximately 0.03 kilometres from an oceanfront pool and dock (fee applies). This two-bedroom, two-bathroom villa sleeps six guests and offers a fully equipped kitchen, air conditioning, a private garden, swimming pool access, complimentary paddleboards and kayaks, and proximity to a second, rentable house ideal for larger groups.
Islamorada, FL
01/07 – 08/07
$468/nighttotal: $3276 (7 )
Condo ∙ 2 Bedrooms ∙ 6 Guests
2 2
apartment , Islamorada, Village of Islands
This two-bedroom flat is located in Angler's Reef, a secure oceanfront community in Islamorada, offering direct beach access and a heated oceanfront swimming pool. This family-friendly accommodation sleeps up to six guests and features a kitchen with a fridge, microwave, and dishwasher, along with air conditioning, a terrace/balcony, garden, and parking.
Islamorada, FL
25/07 – 01/08
$871/nighttotal: $6097 (7 )
Apartment ∙ 2 Bedrooms ∙ 6 Guests
2 5
apartment , Islamorada, Village of Islands
This Islamorada, Florida Keys apartment, located at mile marker 82.2 on Florida Bay, offers direct bayfront access and is a short drive from John Pennekamp Coral Reef State Park, Theatre of the Sea, and Robbie's Marina. The two-bedroom, two-bathroom duplex sleeps six, features a private balcony with Florida Bay views, a fully equipped kitchen, and access to a spa, fitness centre, and parking within a gated one-acre tropical compound.
Islamorada, FL
21/06 – 26/06
$447/nighttotal: $2235 (5 )
Convenient Stay, Superb Location, Free Breakfast
1 2
B&B , Islamorada, Village of Islands
This Islamorada bed and breakfast is situated on the waterfront, just over 160 kilometres south of Miami, offering stunning sunset views over the Florida Keys. The 495 square foot suite comfortably accommodates up to four guests, featuring two queen beds, a living area with a sofa bed, a dining area, and access to a shared swimming pool, kayaks, paddleboards, and other on-site amenities.
Islamorada, FL
25/07 – 01/08
$976/nighttotal: $6832 (7 )
2nd Floor Duplex On Gated Bayfront Property
1 5
apartment , Islamorada, Village of Islands
This Islamorada, Florida Keys apartment, located at Mile Marker 82.2 on Florida Bay, offers direct waterfront access with protected dockage for boats up to 34 feet and is conveniently close to John Pennekamp Coral Reef State Park, Theatre of the Sea, and Robbie's Marina. The two-bedroom, two-bathroom duplex sleeps up to six guests and features a fully equipped kitchen, garden, parking, internet access, air conditioning, and a covered balcony with panoramic Florida Bay views; enjoy relaxing outdoor amenities such as hammocks and a tiki hut within a gated one-acre tropical setting.
9.9 111 reviews
Islamorada, FL
23/07 – 26/07
$629/nighttotal: $1887 (3 )
Swaying Palms Spacious Suite [Ocean Pointe 3201]
2 2
apartment , Tavernier
This Tavernier waterfront apartment, a short 1km stroll from Harry Harris Park and within 5km of Mariners Hospital and Pigeon Key, offers stunning views. The two-bedroom, two-bathroom condo sleeps four, boasting a fully equipped kitchen, free Wi-Fi, a swimming pool, Jacuzzi, tennis court, and private terrace – perfect for families seeking a relaxing Tavernier getaway.
9.6 66 reviews
Islamorada, FL
03/07 – 05/07
$741/nighttotal: $1482 (2 )
Oceanfront Condo Ocean Pointe Suites. Swimming Pool, Beach.
2 5
apartment , Tavernier
This waterfront condominium in Tavernier, Ocean Pointe, is situated at Mile Marker 91 on the ocean side, offering convenient access to John Pennekamp Coral Reef State Park and Windley Key Fossil Reef Geological State Park, just a short drive away. This recently remodelled two-bedroom, two-bathroom apartment, covering 77 square metres and accommodating up to five guests, features oceanfront views, a fully equipped kitchen, in-unit laundry, complimentary Wi-Fi, and access to a shared swimming pool and jacuzzi within a gated resort complex.
Best family friendly Islamorada, FL Short term rentals
Among the 971 accommodations in Islamorada, FL, here are the 4 best family friendly rentals
10 64 reviews
Islamorada, FL
20/06 – 27/06
$574/nighttotal: $4018 (7 )
Charming Cabana-condo In Picturesque Tavernier
2 6
apartment , Tavernier
This two-bedroom apartment is located in Tavernier, Florida, within a 2.4 kilometre walk of Baker's Cay Resort Beach and Harry Harris Park, making it ideal for exploring the area's natural beauty. The property has received excellent user ratings and is perfect for families or groups of friends. The 85 square metre apartment can comfortably accommodate up to six guests and boasts a fully equipped kitchen, air conditioning, and a private garden. Guests can enjoy the on-site swimming pool, Jacuzzi, and tennis court, as well as the nearby beach and other attractions.
10 7 reviews
Islamorada, FL
08/09 – 06/10
$526/nighttotal: $14728 (28 )
Oceanfront Islamorada Townhome- Private Dock, Pool & Pet-friendly
3 4
apartment , Islamorada, Village of Islands
This Islamorada oceanfront apartment, situated in a gated community near the History of Diving Museum and Keys History & Discovery Centre, offers privacy and easy access to local breweries and water sports. The 156 square metre (1679 square foot) property boasts three bedrooms sleeping seven, three bathrooms, a terrace, swimming pool, garden, parking, and features including a fully equipped kitchen, WiFi, and a washing machine.
Islamorada, FL
19/07 – 26/07
$20922/nighttotal: $146454 (7 )
Chateau On The Ocean - The Southernmost Shangrila
1 9
apartment , Islamorada, Village of Islands
This oceanfront estate in Islamorada, Village of Islands, offers direct Atlantic frontage with 120 metres of private beach and a 100-metre private deep-water dock, located approximately 145 kilometres from Miami. This luxury villa accommodates up to 14 guests with 11 bathrooms, featuring a resort-style mosaic pool, a 288 square metre Baccarat-inspired ballroom, a 3,000+ square metre Skyline Terrace with 360° ocean views, and a fitness centre.
10 1 review
Islamorada, FL
24/12 – 02/01
$1803/nighttotal: $16227 (9 )
Brand New Home- Islamorada On Ocean With Views
1 2
apartment , Islamorada, Village of Islands
This three-bedroom, two-bathroom oceanfront property in Islamorada, Village of Islands, boasts direct beach access and is situated near a boat marina. Offering panoramic ocean views, a private pool with a waterfall and poolside bar, a gourmet kitchen with a large island, elevator access, and sleeps up to 15 guests, this brand-new luxury apartment provides unparalleled amenities.
Best Islamorada, FL lodging with a balcony
9.6 224 reviews
Islamorada, FL
18/07 – 22/07
$502/nighttotal: $2008 (4 )
Two Spectacular Ocean Views From The Living Room And Master Bedroom Of The Condo
3 4
apartment , Tavernier
This Tavernier apartment is located just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful beaches and natural attractions of the Florida Keys. It has been rated excellent by previous guests. The apartment has two bedrooms and can comfortably accommodate six guests. It comes with a fully equipped kitchen, a balcony, a swimming pool, a jacuzzi, a sauna, a spa, and parking, providing plenty of space and amenities for a relaxing and enjoyable stay.
9.9 186 reviews
Islamorada, FL
09/07 – 12/07
$714/nighttotal: $2142 (3 )
Ocean View Corner Penthouse Ocean Pointe 5416
2 5
apartment , Tavernier
This penthouse apartment is located in Ocean Pointe Suites, midway between Key Largo and Islamorada in the Florida Keys, offering easy access to both locations, approximately 80km from each. The apartment has received excellent ratings for its location, cleanliness, and overall user experience. The two-bedroom, two-bathroom apartment can comfortably accommodate up to six guests. Amenities include a private beach, pier, marina, swimming pool, jacuzzi, tennis and pickleball courts, and a basketball hoop. Guests can also enjoy direct ocean views from the balcony and living area, and access to a range of water activities such as fishing, diving, snorkeling, paddleboarding, and kayaking.
9.9 189 reviews
Islamorada, FL
18/07 – 22/07
$598/nighttotal: $2392 (4 )
Breathtaking Ocean Views! Owners Who Care. Sangria Sunrise! 10% Off Charters!
1 4
apartment , Tavernier
This Tavernier apartment is directly on the beach, just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park. The property has received excellent ratings for location, cleanliness, and overall experience. The apartment is a one-bedroom, one-bathroom property with a floor area of 56 square metres, suitable for up to four guests. Amenities include a fully equipped kitchen, a swimming pool, a jacuzzi, a terrace, a garden, and parking.
Islamorada, FL
08/09 – 06/10
$305/nighttotal: $8540 (28 )
Condo ∙ 2 Bedrooms ∙ 4 Guests
2 4
apartment , Islamorada, Village of Islands
Beacon Reef #503, a two-bedroom condo in Islamorada, Village of Islands, is situated at mile marker 83.2, offering easy access to local restaurants and fishing/diving opportunities. This fifth-floor apartment boasts ocean views, sleeps four guests, includes a king-size bed, two full-size beds, two bathrooms, a private balcony, and access to a swimming pool, hot tub, fitness centre, and other Beacon Reef amenities.
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What are the best short term rentals in Islamorada, FL?
Bay Harbour Islamorada Oceanfront Views 3/2.5 Updated Condo Dock
3 2
apartment , Islamorada, Village of Islands
This waterside condominium is located in the gated Bay Harbour community at mile marker 77.5 bayside in Matecumbe, Islamorada, within 1.6 kilometres of Anne's Beach and the San Pedro Underwater Archaeological Preserve State Park. This three-bedroom holiday flat, accommodating up to six guests, offers a private screened terrace with ocean views, a gourmet kitchen, a private 9.45-metre protected dock with a boat lift, and on-site access to a swimming pool and spa.
9.4 70 reviews
Islamorada, FL
09/10 – 12/10
$431/nighttotal: $1293 (3 )
Marina To Ocean View Key Largo Ocean Pointe 5308
2 2
apartment , Tavernier
This Tavernier waterfront apartment, situated 1.1 kilometres from Harry Harris Park and within 4.8 kilometres of Mariners Hospital and the Florida Keys Dive Centre, offers stunning views. The 84 square metre property features three bedrooms, two bathrooms, a sofa bed for a total guest capacity of four, and includes a fully equipped kitchen, private balcony, swimming pool, jacuzzi, and parking.
9.8 53 reviews
Islamorada, FL
24/07 – 26/07
$679/nighttotal: $1358 (2 )
Unbeatable Views From Lux Oceanfront Suite
2 2
apartment , Tavernier
This Tavernier waterfront apartment, a short walk (under 2.4km) from Baker's Cay Resort Beach and Harry Harris Park, and within 5km of Mariners Hospital and the Florida Keys Dive Centre, offers stunning views. The 85 square metre property features two bedrooms, two bathrooms, sleeps four, and includes a fully equipped kitchen, swimming pool, jacuzzi, tennis court, and free Wi-Fi.
9.7 287 reviews
Islamorada, FL
23/07 – 26/07
$573/nighttotal: $1719 (3 )
Keys Deal W/cafe & Pool Bar! Up To 20% Off Oceanfront 2/2 With Private Beach
2 2
apartment , Tavernier
This Tavernier apartment is conveniently located just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's attractions. The property has received excellent ratings for user experience, location, and cleanliness. The two-bedroom apartment spans 79 square metres and comfortably accommodates up to four guests. It features a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a terrace, a garden, a spa, a tennis court, and parking.
Best Islamorada, FL lodging with laundry available
Islamorada, FL
03/07 – 05/07
$799/nighttotal: $1598 (2 )
Key Largo 2br Condo - Ocean View, Pool, And Beach
2 5
apartment , Tavernier
This Tavernier oceanfront apartment, near Key Largo and Islamorada, offers direct beach access and proximity to John Pennekamp Coral Reef State Park and Jacob's Aquatic Centre. The 79-square-metre (850-square-foot) property features two bedrooms, two bathrooms, sleeps six, and includes a kitchen with fridge, microwave, and dishwasher, plus a swimming pool and parking; on-site resort amenities such as a junior Olympic-sized swimming pool and tennis courts are also available.
9.8 241 reviews
Islamorada, FL
24/07 – 26/07
$778/nighttotal: $1556 (2 )
Luxurious Suite+open Ocean Views+pool & Cabana Bar
2 2
apartment , Tavernier
This waterfront apartment is located in Tavernier, just a short walk from Baker's Cay Resort Beach and Harry Harris Park, offering a peaceful and relaxing atmosphere. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience. The apartment is spacious, covering 85 square metres and comfortably accommodating up to six guests. It features a fully equipped kitchen, a washing machine, a balcony, a Smart TV, and access to a swimming pool, spa, tennis court, and barbecue grills, ensuring a comfortable and enjoyable stay.
10 1 review
Islamorada, FL
30/07 – 06/08
$536/nighttotal: $3752 (7 )
Ocean Front Townhouse With Breathtaking Views!
1 2
apartment , Islamorada, Village of Islands
This oceanfront townhouse in Islamorada, Village of Islands, boasts direct beach access and is conveniently located near local restaurants and water activities, though precise distances aren't specified. Sleeping seven comfortably, this two-bedroom, one-bathroom property features a king-size bed, daybed, and pull-out sofa, a fully equipped kitchen, and access to a gated community with a heated pool and fishing pier; towels and linens are provided.
9.6 20 reviews
Islamorada, FL
09/08 – 14/08
$576/nighttotal: $2880 (5 )
Bungalow #5 - 2 Bed/1 Bath & Pool In Islamorada
2 2
apartment , Islamorada, Village of Islands
This charming bungalow is situated in the Matecumbe neighbourhood of Islamorada, within easy reach of Bud n' Mary's Dive Center and Florida Keys Brewing Co., offering a peaceful retreat in a vibrant area. It has consistently received excellent user ratings, making it a popular choice for travellers. The bungalow features two bedrooms and one bathroom, providing comfortable accommodation for a small family or group of friends. Guests can enjoy a private backyard, a community heated pool, and the convenience of air conditioning, internet access, and pet-friendly policies.