
Holiday rentals with a pool in Islamorada
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Top-rated rentals with a pool in Islamorada
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 68 acres and one side is surrounded by a nature preserve.

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

Escape to the Seaside - Tiburon Cottage
Our one bedroom suite features separate bedroom and living areas, giving you the space and comfort to relax, sleep and eat. Set yourself up in a large in-suite space with private entrance. The suite provides all the comforts of home. Unpack and stretch out in a stylish suite with a sofa, flat screen TV, complimentary Wi-Fi and premium cable programming or explore all the Keys have to offer. Here, you’ll have everything you need, because to us it’s not a temporary accommodation, it’s your home.

Your Happy Place - Oceanfront
Experience the ultimate coastal getaway at Ocean Point in the Florida Keys. Nestled along the Atlantic Ocean, our 2 bed/2 bath condo offers unrivaled ocean views from the moment you step inside. Indulge in the array of amenities available at our property including a private beach, pier, marina, snorkeling, family pool and a full service restaurant. Our condo comfortably sleeps 6-7 guests. Equipped with full kitchen and washer/dryer, we provide all the conveniences for a seamless stay.

Oasis2 in Key Largo With a million dollar view
Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

Waterfront Home 37.5-ft dock, Cabana Club Included
Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Oceanfront Breeze, Stunning Views, Beach/Pool
Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Blue Haven Key Largo | Ocean Pointe 1315
Tastefully decorated and newly renovated 2 Bedroom & 2 Bathroom Condo with a wonderful view of Florida Keys Nature. Relax and escape to this beautiful getaway in the heart of Tavernier, ideally located between Key Largo & Islamorada. The property itself has amenities galore: sparkling pool with hot tub and newly re opened POOL BAR, boat ramp and marina, tennis courts which convert into pickle ball courts, beach with pier, free parking and charcoal grills to cook your catch!

New Aqua Lodge 2Beds 1 Bath with Full Kitchens
This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Ocean views at “Sangria Sunrise” 10% off Charters
Welcome to Sangria Sunrise at Ocean Pointe Suites in the beautiful Tavernier Key Florida. Relax and enjoy all of the options offered such as Jr. Olympic sized pool, beach, marina, kayak rentals, tennis courts, and so much more! We invite you to come stay at this cozy and updated one bedroom and one bathroom top floor condo with the most amazing ocean views. We offer a very comfortable queen sized bed and also a queen sleeper sofa that's equally as comfortable.

2br/1ba w heated pool, 1 mile to robbies marina
Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

Key Largo! Tavernier! Welcome to Paradise!
A perfect tropical getaway! Life is good today! Bright, airy, 500 plus sq ft., canal front studio, close to the bay. From the dock you can KAYAK to mangrove tunnels, fish, or just relax. Cold drink in your hand, life is good today! You are going to have an awesome vacation!! ( NOTE: THE POOL MAY BE SHARED ON OCCASION, WITH OUR FAMILY. A SIGNED LIABILITY RELEASE IS REQUIRED AT CHECK IN )
Popular amenities for Islamorada rentals with a pool
House rentals with a pool

Tiny Home on Waterfront | Bay Views | Deck | Pool

Sea Ray Cove w/ 80' Dock, Pool, Beach & Tiki Hut

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

NEW! CASA LARGO -Golf Cart, 2 Kings 3 Bath, Kayaks

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

Mariners 212 Great Location with Marina Views

Waterfront House with 37 ft Dock & Cabana Club

Bayview Beautiful townhouse in Islamorada, FL KEYS
Condo rentals with a pool

1BR - Key Largo Sun & Sand Hideaway

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Beachside Unit 14 - Brand New Kitchen and Bathroom

Condo in Tavernier

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

🏝 Oceanfront Paradise Awaits You

Tropical Getaway

3212 Across from Pool * King & Queen/Twin Bunk Bed
Other holiday rentals with a pool

Coastal Oasis #44 Key Largo 4BR Villa | Partial

Tiki Hut w/TV, Pool, Kayak, Paddleboards, Bikes!

Islamorada bungalow 2 bed & pool

Angler’s Reef home • Pool • Kayaks • Paddle boards

Discount - Jan 31! 3 Bed/3 BA Cabana Club Access!

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom

Oceanfront 3‑Stories of Bliss • Dockage & Gameroom

Gone Coastal @ Ocean Pointe
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $617 NZD | $723 NZD | $750 NZD | $617 NZD | $837 NZD | $602 NZD | $706 NZD | $614 NZD | $607 NZD | $525 NZD | $554 NZD | $604 NZD |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
Quick stats about holiday rentals with a pool in Islamorada

Total holiday rentals
Explore 620 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at $117 NZD per night before taxes and fees

Verified guest reviews
Over 4,040 verified reviews to help you choose

Family-friendly holiday rentals
420 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 320 rentals that welcome pets

Rentals with dedicated workspaces
390 properties have a dedicated workspace

Wi-Fi availability
620 of Islamorada holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Islamorada rentals

4.7 Average rating
Islamorada stays receive an average rating of 4.7 out of 5 from guests
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Calusa Beach & Loggerhead Beach
- Coral Castle
- Sea Oats Beach
- Schnebly Redland's Winery & Brewery
- Long Beach
- Everglades Alligator Farm
- Conch Key
- Bahia Honda State Park
- Theater of the Sea
- Homestead-Miami Speedway
- Monkey Jungle
- Key Largo Kampground And Marina
- Seven Mile Bridge
- Calusa Campground
- Sunset Park
- Robbies Marina Of Islamorada
- Dolphin Research Center
- Florida Keys Aquarium Encounters
- Founder's Park




