Key Largo Listings

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Monthly Rent $2875 - $3725

Bayfront townhouse located in the lush tropical setting of Rock Harbor Club. Key Largo, Florida, Listing ID: 24303

MINIMUM STAY: 28 Nights. Bayfront townhouse located in the lush tropical setting of Rock Harbor Club in Key Largo. You'll love the open water views from the two oversized screened balconies - one off the main living area and the other off the master suite. There's something...

  • Home
  • 1000-1200
  •  2
  •  2 1/2
Monthly Rent $3800 - $4850

3 BR Townhouse Oceanside with 30' Dock and Boat Lift Key Largo, Florida, Listing ID: 24304

Minimum Rental: 1 MONTH This is a gorgeous 3 bedroom townhouse in a private upscale ocean front condominium community! Everything you could want is located within the community - heated pool; hot tub; covered seating area; tennis court; children's playground;...

  • Condo
  • 2261
  •  3
  •  2
Monthly Rent $8500 - $9950

!Exceptional Home Designed for Tropical Living Pool Boat Dock Tropical Setting!! Key Largo, Florida, Listing ID: 24316

MINIMUM STAY: 1 MONTH Exceptional single family home designed for tropical living - charming interior and extraordinary outdoor living areas. Open concept living area on the middle level of the home offers a formal dining with 8 chairs and 3 bar stools at the kitchen counter....

  • Home
  • 2000-2500
  •  4
  •  4
Monthly Rent $3175 - $3525

Key Largo's Finest Bay Front Condominium Complexes Beautiful View of Florida Bay Key Largo, Florida, Listing ID: 24317

MINIMUM STAY: 7 NIGHTS. This 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite counters, new cabinetry and appliances. New linens...

  • Condo
  • 800-1000
  •  2
  •  1 1/2
Monthly Rent $4750 - $5200

Water views from almost every room in this home! Key Largo, Florida, Listing ID: 25022

Minimum Rental: 28 Days "Casa Kai" has water views from almost every room in this home! Gaze at the water from your bedroom, the dining area, the balcony, or the Tiki! This home is so close to open water you almost feel like it is on the open water. The expansive ocean...

  • Home
  • 1800-2000
  •  4
  •  2
Monthly Rent $5400 - $7200

Home Away From Home, Cozy 3 Bedroom Key Largo Beach House Key Largo, Florida, Listing ID: 25700

A cozy 3 bedroom / 1 bathroom Key Largo home with great views of the beautiful Gulf Coast. Just steps away from the water. You can sit and relax in the screened in patio and enjoy some great amenities including 2 KAYAKS that you can use to go into canals that are close by to see...

  • Beach Home
  • 1500
  •  3
  •  1
Monthly Rent $1700 - $2800

Bayfront home with shared pool, tennis on-site, shared boat ramp! Key Largo, Florida, Listing ID: 26000

Kick off your shoes and leave your worries behind when you book your next seaside getaway to this bayfront Key Largo home. Boasting shared amenities like a pool, tennis courts, and a community boat ramp, your stay promises to be stress-free. Set on the north shore of Key...

  • Home
  • 778
  •  2
  •  2
Monthly Rent $2900 - $3500

Waterfront getaway with private dock - great for fishermen and boaters! Key Largo, Florida, Listing ID: 26001

Surround yourself with water views and canal-front convenience when you book your next stress-free getaway to this Key Largo retreat. Boasting views from nearly every window and private dock slipping into vacation mode will be a breeze. Set near the calm waters of Florida's...

  • Home
  • 1800
  •  3
  •  2 1/2
Monthly Rent $3100 - $4400

Bright and cheery family-friendly home w/soaking tub, dock access, & ocean views Key Largo, Florida, Listing ID: 26003

Get the whole group together for a sun-soaked getaway they'll never forget when you book a trip to this waterfront Key Largo home. Boasting ocean views, easy beach access, and room for up to nine guests, this family-friendly gem will make sure that you enjoy your well-deserved...

  • Home
  • 5912434
  •  4
  •  2 1/2
Monthly Rent $3000 - $3500

Fully furnished, 2/1 downstairs apt on the clearest canal in the upper Florida Keys!! Remodeled less than 1 year ago. Key Largo, Florida, Listing ID: 26495

Beautifully remodeled ground floor apartment, perfect for two people with occasional guests. One bedroom is furnished with a queen bed, the other is furnished with two twin beds. There is a brand new (delivered 9/20) queen sleeper sofa in the living room. This apartment features...

  • Home
  • 850
  •  2
  •  1

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Monthly Rent $3000 - $3200

Now renting 2019- Waterfront Bright Modern interior! Beautiful 2 BR 2 BA Condo Heated Pool Fort Myers, Florida, Listing ID: 23303

3200 per month includes all taxes, utilities, cable peak season. Building with elevators for you convenience. Plan now for 2019. Beautiful tropical grounds nestled on the Caloosahatchee River. Quartz counters in kitchen and baths. Beautifully fully renovated condo. Condo is...

  • Home
  • 1000-1200
  •  2
  •  2
Monthly Rent $1600 - $2800

Monthly Getaway - Relax in Tranquility, Tropical Breeze & Beach! Lauderdale By The Sea, Florida, Listing ID: 24239

This is a pristine 1-bedroom condo fully furnished and perfect for a long relaxing getaways. The unit is beautifully accessorized with beach decor and furnishings. The amenities include free high speed internet, cable, flat screen TVs, fresh linens, towels and full kitchen...

  • Condo
  • 300-600
  •  1
  •  1

MIAMI BEACH/Great area on the Beach centrally located. Fully equipped, gated parking, 24hr security. All inclusive rate! Miami Beach, Florida, Listing ID: 24261

This apartment is FULLY EQUIPPED! Very clean and nicely decorated. The Kitchen is totally equipped with all your needs and more. Full size refrigerator, 4 burner stove and microwave/convection oven. (Coffee maker, Toaster, Toaster Oven, Blender, Panini Grill, Ice Maker). ...

  • Condo
  • 300-600
  •  0
  •  1
Monthly Rent $12000

Beach Front Home, With Private Sandy Beach, Just what you have been looking for! Islamorada, Florida, Listing ID: 24285

MINIMUM STAY: 29 DAYS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family home with a private sandy beach in the Keys. This home is new to the rental market. It is located in a highly desirable area of Islamorada on a dead end street. ...

  • Home
  • 2000-2500
  •  3
  •  2
Monthly Rent $5500 - $7500

Great Private Home with Spectacular Views of the Ocean from anywhere in Home!!!! Islamorada, Florida, Listing ID: 24289

Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room...

  • Home
  • 1200-1400
  •  3
  •  3
Monthly Rent $3675 - $4750

"Meticulously" cared for Home the owners are now offering to share for your Vac! Islamorada, Florida, Listing ID: 24293

MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 4-6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering...

  • Home
  • 1000-1200
  •  2
  •  2
Monthly Rent $2575 - $4000

Exceptional Condo, Gated Ocean front Condo Complex with Swimming Pool, Hot Tub! Islamorada, Florida, Listing ID: 24295

MINIMUM STAY: 29 DAYS Exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen with...

  • Condo
  • 800-1000
  •  2
  •  2
Monthly Rent $4400 - $5250

Extraordinary ocean front condo with panoramic views of the Atlantic Ocean!!! Islamorada, Florida, Listing ID: 24301

Minimum Rental: 1 Month Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. It...

  • Condo
  • 1200-1400
  •  2
  •  2
Monthly Rent $4400 - $5300

Oceanfront 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Islamorada, Florida, Listing ID: 24302

Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. PHOTO UPDATES COMING SOON. "Beacon Reef 522" offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying one month or more you...

  • Condo
  • 1275
  •  2
  •  2
Monthly Rent $4950

Stay in the Florida Keys! You will love this wonderful 2013 built stilt home!!!! Plantation Key, Florida, Listing ID: 24310

MINIMUM STAY: 30 DAYS NEW HOME (2013) Spend the fall or winter in the Florida Keys! You will love this wonderful 2013 built stilt home. Features include an open living area with gourmet kitchen, stainless steel appliances, including a wine refrigerator and granite...

  • Home
  • 1400-1600
  •  3
  •  2
Monthly Rent $5950 - $7950

The Florida Keys at its best.3 Bedrooms and 2 Plantation Key, Florida, Listing ID: 24311

MINIMUM STAY: 28 DAYS NEW OPPORTUNITY to LIVE THE LIFE! This 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best.  Conveniently located on a deep and wide canal with easy access to...

  • Home
  • 2000-2500
  •  3
  •  2 1/2
Monthly Rent $4000 - $7500
Monthly Rent $1600 - $2200

Longing for the radiant sunshine, magnificent sunsets and serenity of Florida's Fort Myers, Florida, Listing ID: 25040

Whether for a month or for a whole season, Fort Myers Condos, a unique resort on the west coast of Florida, will make your wish come true. Strategically located less than 3 km from downtown Fort Myers, between Tampa and Naples, each condo is situated directly on the banks of...

  • Condo
  • 1200-1400
  •  2
  •  2
Monthly Rent $3300 - $4600

Beautiful Views Most Desirable Unit in the Upper Keys Near Everything Fish Swim! Islamorada, Florida, Listing ID: 25067

NEW ON THE RENTAL MARKET - Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself...

  • Condo
  • 1200-1400
  •  2
  •  2
Monthly Rent $6500 - $7500

THE GORGEOUS POOL, HOT TUB, and TIKI BAR are ready and waiting SENSATIONAL HOME Plantation Key, Florida, Listing ID: 25068

MINIMUM STAY: 29 DAYS Sensational remodeled single family home on Plantation Key awaits your arrival. The gorgeous POOL, HOT TUB, and TIKI BAR are ready and waiting. Imagine fun filled days and evenings relaxing in the patio and yard area! The patio is spacious and...

  • Home
  • 1800-2000
  •  4
  •  3
Monthly Rent $4500

Charming 2 Bed 2 Bath Open Living Area Large Kitchen Boat Dock Overlooking Canal Plantation Key, Florida, Listing ID: 25069

Minimum Stay 1 Month. "Beba's Reef House" will capture your imagination the moment you enter the home and rise to the main living level through the reef painted on the walls of the stair well and the photos of fish captured by the owner during numerous dives here in the...

  • Home
  • 1400-1600
  •  2
  •  2
Monthly Rent $4500

Ground floor 3 bedroom condo ,situated near Bonita Beaches. Gated community Naples, Florida, Listing ID: 25318

Our property overlooks a lake, fountain and small waterfall. It is situated in lush grounds well tendered gardens. It is very peaceful even in high season. The property it self is furnished and well maintained to a very high standard. There are 9 local beaches the nearest...

  • Condo
  • 1200-1400
  •  3
  •  2

Fully Remodeled & Furnished 3/2 modern villa right off the beach in Fort Lauderdale Fort Lauderdale, Florida, Listing ID: 25646

Welcome home! Relax in this Fully Remodeled & Furnished 3/2 modern villa right off the beach in highly-sought-after Fort Lauderdale Beach. Well equipped & tastefully decorated w brand new kitchen & SS appliances, 2 Queen beds, 1 King bed, TVs in all rooms. Minutes to Downtown Ft...

  • Villa
  • 1400
  •  3
  •  2
Monthly Rent $5200

harming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! Islamorada, Florida, Listing ID: 25667

MINIMUM RENTAL 1 MONTH Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom ...

  • Home
  • 1494
  •  3
  •  2
Monthly Rent $2600

AVAILABLE NOW Key Biscayne, Florida, Listing ID: 25712

Beautiful Key Biscayne Florida 195 Sunrise Drive Apt 7 Excellent Location on the Key. This is a comfortable one bedroom one guest room/office beach condo. New kitchen updated throughout. Corner unit. You have access to a private beach and park 2 blocks away from building (fob...

  • Condo
  • 890
  •  2
  •  1
Monthly Rent $2200 - $6000

Ocean views, shared pool & hot tub! Walk to the beach - snowbirds welcome! Bonita Springs, Florida, Listing ID: 25740

Escape to the sugar-sand paradise of Florida at this Bonita Springs vacation rental. Work on your tennis game, relax poolside, and play shuffleboard with your group of up to four guests! Just a short distance from white sand beaches, this home is a great choice for those...

  • Condo
  • 508
  •  1
  •  1
Monthly Rent $4500 - $6400

Cozy, waterfront getaway w/ furnished lanai & private, heated pool & hot tub Bonita Springs, Florida, Listing ID: 25745

Plan to enjoy your next vacation in southwest Florida at this beautiful four-bedroom escape with deluxe amenities like a private pool and hot tub, a canal side dock, a screened and furnished lanai, and space for up to nine lucky guests. The city of Bonita Springs is home to...

  • Home
  • 2414
  •  4
  •  3
Monthly Rent $3300 - $4500

Hacienda Village - Townhome w/ a shared pool, activities, & nearby beaches - snowbirds welcome! Bonita Springs, Florida, Listing ID: 25941

Grab a few best friends or your family and treat them to a memorable vacation at this Bonita Springs condo. A two-bedroom, two-bathroom townhouse, it's perfect for up to four guests and offers fabulous amenities, including a community swimming pool, shuffleboard and tennis...

  • Home
  • 1528
  •  2
  •  2 1/2
Monthly Rent $1700 - $3500

Quiet condo w/ shared pool - easy access to beach & golf Fort Myers, Florida, Listing ID: 25962

For your next Florida vacation, consider this elegant Fort Myers condo! With access to a shared pool and world-class golf courses at your fingertips, a stay in this classy condo practically guarantees relaxation. Nestled in the quiet Palmetto Cove community, this condo is...

  • Condo
  • 1448
  •  3
  •  2
Monthly Rent $1600 - $3200

Modern condo w/ shared pool, entertainment - drive to golf & beach Fort Myers, Florida, Listing ID: 25964

Escape to Fort Myers for a relaxing time in the sun at the two-bedroom condo. With a shared pool, entertainment, and easy access to a number of golf courses nearby, up to four guests will make memories here! Located in the quiet community of Palmetto Cove, you'll have...

  • Condo
  • 1125
  •  2
  •  2
Monthly Rent $1700 - $3200

Family-friendly condo w/ shared pool - close to downtown & the beach Fort Myers, Florida, Listing ID: 25965

The whole family will fall in love with Fort Myers when you stay at this comfortable two-bedroom condo. Offering a convenient location close to downtown and white sand beaches, plus access to a community pool, up to four guests can call this place home. Located in a quiet...

  • Condo
  • 1072
  •  2
  •  2
Monthly Rent $1500 - $3000

Waterfront condo w/ shared pool & entertainment - close to beach & golf! Fort Myers, Florida, Listing ID: 25968

Palm trees, beaches, and world-class golf await at this waterfront condo in Fort Myers! Offering access to a shared pool and entertainment, up to two guests will make memories in this one-bedroom home. Part of a peaceful community that's conveniently close to the highway,...

  • Condo
  • 623
  •  1
  •  1
Monthly Rent $1600 - $3600

Family-friendly townhouse w/ shared pool - close to golf, beach & more! Fort Myers, Florida, Listing ID: 25969

Come for an exceptional stay in Fort Myers at this three-bedroom townhouse with room for the whole family. Offering access to a shared pool as well as golf courses and beaches nearby, up to six guests will love it here. Part of the Sail Harbor community just a short drive...

  • Condo
  • 1819
  •  3
  •  2 1/2
Monthly Rent $2500 - $3900

Comfy townhouse w/ shared pool & on-site tennis - next door to Founders Park! Islamorada, Florida, Listing ID: 25997

Slip away to the turquoise waters and warm sands of the Florida Keys with a stay at this charming Islamorada townhouse! Located right next door to Founders Park, which boasts a public beach and marina, this sunny vacation rental also includes access to a shared pool and tennis...

  • Home
  • 1400
  •  2
  •  2
Monthly Rent $5000 - $10600

Cozy, chic cottage w/ private pool - close to beach and dog friendly, too! Key West, Florida, Listing ID: 26007

Make this cozy and chic Key West cottage your home away from home for your next Florida vacation, and revel in a private pool, deck, and covered back porch, as well as close proximity to the beach. And the real bonus: you can bring your favorite canine friend along,...

  • Home
  • 1400
  •  3
  •  2
Monthly Rent $7200 - $15000

Welcoming home w/ private pool & covered porch - walk to dining & attractions Key West, Florida, Listing ID: 26008

Head to the Keys for your next Florida getaway and set yourself up for comfort and convenience when you stay at this welcoming, well-equipped home with a private pool and charming covered porch. You'll be situated only a mile from South Beach, so the sand and water are...

  • Home
  • 1440
  •  3
  •  3
Monthly Rent $6150 - $16350

Historic home in Old Town w/ private pool & detached cottage - dogs OK Key West, Florida, Listing ID: 26011

Come experience Key West in all its glory when you stay in this dog-friendly historic home featuring a private pool and lush tropical gardens. Your group of up to six will be set for a comfortable and convenient stay, and the detached cottage is the perfect spot for the teenager...

  • Home
  • 1599
  •  3
  •  3
Monthly Rent $5000 - $13000

Dog-friendly home w/ private pool & space to lounge - walk to everything! Key West, Florida, Listing ID: 26013

Come to Key West and ensure your Floridian getaway is the best it can be when you make this desirable rental your home away from home. Your group of up to eight will experience tranquil comfort and tasteful style in this dog-friendly home with a private pool, luxurious patio...

  • Home
  • 1596
  •  3
  •  3 1/2
Monthly Rent $4600 - $12100

Dog-friendly home w/ private pool, jetted tub, & gardens - relax on a hammock! Key West, Florida, Listing ID: 26015

If you're headed to Key West, make the most of your vacation and stay in this comfortable dog-friendly home with a private pool, a jetted tub, and gardens for an unforgettable Florida experience. You'll be located in a quiet neighborhood in New Town and only a bike ride or...

  • Home
  • 1646
  •  3
  •  2
Monthly Rent $5100 - $14250

Dog-friendly home w/ private pool - walk to parks, shopping, & the beach! Key West, Florida, Listing ID: 26017

This Key West home is waiting for you and your group of up to six to come make yourselves at home and enjoy lazy days by your private pool. You'll be within easy reach of the beach, parks, and all the necessities. Walk to Higgs Beach and the pier, Indigenous Park, and dinner...

  • Home
  • 1672
  •  3
  •  3
Monthly Rent $4750 - $12870

Dog-friendly, comfortable home w/ shared pool - close to beaches & attractions Key West, Florida, Listing ID: 26019

Head to Key West and revel in access to a shared pool, dog-friendly accommodations, and close proximity to beautiful beaches and major attractions when you stay at this three-bedroom, three-bath home for six. This rental is located in the heart of Old Town, putting you one...

  • Home
  • 1455
  •  3
  •  3
Monthly Rent $6000 - $13400

Dog-friendly, cozy home w/ private pool & hot tub - walk to must-see attractions Key West, Florida, Listing ID: 26021

If Key West is on your travel itinerary, make this lovely dog-friendly rental for six your home away from home and spend your time lounging by your private pool and spa. Located in Historic Bahama Village, this home is one block away from the world-famous Duval Street, where...

  • Home
  • 0
  •  3
  •  2
Monthly Rent $4400 - $10200

Stylish, inviting home w/private pool in heart of downtown - walk to everything! Key West, Florida, Listing ID: 26043

Make this stylish, three-bedroom, two-and-a-half bath home for six yours when you come to Key West, and revel in amenities like a private heated pool and an ideal location. Located in downtown Key West, this home is a mere one block from Duval Street. Southernmost Point and...

  • Home
  • 1178
  •  3
  •  2 1/2
Monthly Rent $7900 - $11500

Comfortable, waterfront home w/ covered lanai, pool, Jacuzzi tub - lovely views Key West, Florida, Listing ID: 26044

This comfortable, four-bedroom, three-bath home in Key West offers a private covered lanai and pool, as well as lovely views from the balcony and a Jacuzzi tub. The home is located in quiet Key Cove Landings community, within walking distance to grocery shopping, restaurants,...

  • Home
  • 2347
  •  4
  •  3
Monthly Rent $7900 - $11500

Waterfront home w/ private pool, Jacuzzi, balcony w/ sweeping ocean views Key West, Florida, Listing ID: 26046

Escape to Key West and stay in this lovely waterfront home for a luxurious getaway. Your group will enjoy a private pool, a Jacuzzi tub, and a balcony with sweeping ocean views. You'll be centrally located in the heart of Key West in the exclusive Key Cove community. Walk to...

  • Home
  • 2450
  •  4
  •  3 1/2
Monthly Rent $8200 - $12000

Inviting, waterfront home w/ private pool, Jacuzzi, & balcony w/ ocean views Key West, Florida, Listing ID: 26048

This lovely four-bedroom, four-bath home for 10 provides a prime location and excellent amenities, including a private pool, a Jacuzzi, and a covered balcony with sweeping ocean views. You'll be located on the north side of Key West in the exclusive Key Cove community. Walk...

  • Home
  • 2400
  •  4
  •  4
Monthly Rent $7900 - $11500

Cozy, waterfront home w/ private pool & Jacuzzi - near all major attractions! Key West, Florida, Listing ID: 26050

Luxury awaits in this cozy yet spacious four-bedroom, four-bath Key West home, featuring a private pool and Jacuzzi, as well as close proximity to all the major locations. It's ideal for multiple families and large groups offering accommodations for up to 10. You'll enjoy...

  • Home
  • 1725
  •  4
  •  4
Monthly Rent $8000 - $11800

Elegant, waterfront home w/ private pool and covered deck with ocean views Key West, Florida, Listing ID: 26051

Let this elegant, waterfront rental in Key West serve as home base for your next Florida vacation, and enjoy a private pool and covered deck with ocean views, among other fine amenities. The rental is located in the private community of Key Cove Landings within walking...

  • Home
  • 2691
  •  4
  •  3 1/2
Monthly Rent $7900 - $11500

Roomy waterfront home w/ private pool, lanai, & deck - views from every window! Key West, Florida, Listing ID: 26053

This four-bedroom, three-and-a-half-bath Key West home has a private heated pool, a covered lanai, and an upper deck, as well as beautiful views from every window. It's situated in the exclusive Key Cove Landings, right on the water and within walking distance to grocery...

  • Home
  • 2691
  •  4
  •  3 1/2
Monthly Rent $6800 - $12100

Spacious home w/ private pool - close to attractions & beach, dog OK! Key West, Florida, Listing ID: 26055

Escape to Florida and stay in this private dog-friendly home for six for your Key West retreat and enjoy a private pool, wraparound deck, and patio. You'll be tucked away in a quiet Key West neighborhood, surrounded by lush foliage, and you'll be within walking distance of...

  • Home
  • 1854
  •  4
  •  3 1/2
Monthly Rent $5300 - $10900

New home w/ private pool & rooftop patio - ideal location & steps from beach! Key West, Florida, Listing ID: 26058

This four-bedroom, three-and-a-half bath Key West home has just what you and your group of up to eight need for an awe-inspiring Florida beach getaway, including a private heated pool, rooftop patio, and easy access to the beach and major attractions. You'll be a few steps...

  • Home
  • 1912
  •  4
  •  3 1/2
Monthly Rent $9300 - $13500

Home w/private pool & hot tub - walk to everything Key West, Florida, Listing ID: 26060

Sink into the comfort of this lovely Key West home for 10, and enjoy a luxurious Florida getaway, complete with private pool and hot tub and excellent location, allowing you to walk to dining and all the sights. This home is located on a quiet street in Old Town Key West, a...

  • Home
  • 2352
  •  4
  •  3 1/2
Monthly Rent $6100 - $11300

Spectacular, oceanfront, dog-friendly home w/ private pool & boat docks Key West, Florida, Listing ID: 26063

Bring your large group of up to 18 to Key West and stay in this spectacular five-bedroom, three-bath oceanfront home for an unforgettable Florida vacation. Amenities include a private pool, massive deck with seating, lush surrounding gardens, and two private docks, as well as...

  • Home
  • 3332
  •  0
  •  
Monthly Rent $10700 - $19500

Dog-friendly home on a private beach with private pool & hot tub Key West, Florida, Listing ID: 26066

Experience the best of the Keys during a stay in this oceanfront home with dog-friendly accommodations (for a nightly pet fee) and a private pool and hot tub! Shark Key Chateau offers room to bring the whole family along. While you'll feel like you're on your own private...

  • Home
  • 4651
  •  5
  •  4 1/2
Monthly Rent $5400 - $11800

Spacious, canal front villa w/ private pool and hot tub - 3 dogs are welcome! Summerland Key, Florida, Listing ID: 26068

Stay in this three-bedroom, two-bath canal front villa for six when you come to Summerland Key and revel in rest and relaxation with your very own private pool and hot tub. And to make your vacation complete, you can bring three dogs along for a small nightly fee! This...

  • Villa
  • 1650
  •  3
  •  2
Monthly Rent $4100 - $8400

Dog-friendly, cabana-style cottage w/ private pool - two blocks from town! Key West, Florida, Listing ID: 26069

Escape to Key West for a fun, action-packed getaway when you stay in this two-bedroom, one-and-a-half bath cabana-style cottage for six and enjoy a private pool and easy access to all the action. Bring along the family dog, too, for a small nightly fee! This home is located...

  • Home
  • 606
  •  2
  •  1 1/2
Monthly Rent $4100 - $8400

Cozy, dog-friendly home w/ patio & private pool - walk to dining & shopping! Key West, Florida, Listing ID: 26071

Head to Key West for a rejuvenating reprieve and enjoy the patio and private pool at this cozy, two-bedroom home conveniently situated near dining, shopping, and all the must-see sights. Your beloved family dog is also welcome for a small nightly fee. You'll be about two...

  • Home
  • 792
  •  2
  •  2
Monthly Rent $3000 - $6150

Dog-friendly condo in prime location - walk to dining & sights, near the beach! Key West, Florida, Listing ID: 26073

Get away from it all and head to Key West for a sun-filled vacation with this two-bedroom, two-bath condo for six and enjoy easy access to restaurants, attractions, and the beach. You can also bring your beloved dog along for a small nightly fee! You'll be located on the...

  • Condo
  • 0
  •  2
  •  2
Monthly Rent $2500 - $6700

Welcoming, conveniently-located, dog-friendly home - walk to everything! Key West, Florida, Listing ID: 26074

If Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and enjoy comfort and the benefit of being right in the heart of the island. You'll be in the center of Key West within walking distance to restaurants, bars, and shops, as well...

  • Home
  • 705
  •  1
  •  1
Monthly Rent $4400 - $12000

Fully-renovated home w/ yard, porch, shared pool - one block from Duval Street Key West, Florida, Listing ID: 26075

Originally built in 1933, this fully renovated, three-bedroom home has a yard, a cozy front porch where you can sit back and watch the day go by, and room for up to eight guests (six comfortably). Stroll to shopping, entertainment, and beaches, all within a few blocks of this...

  • Home
  • 1051
  •  3
  •  2
Monthly Rent $2500 - $7500

Enchanting seaside cottage w/private pool, off-street parking, & prime location Key West, Florida, Listing ID: 26080

Come explore the rich history, decadent beaches, and seaside dining spots when you book your getaway to this Key West cottage. Filled with charm for up to five guests to enjoy, this home offers off-street parking, a private pool, and a location that puts you close to all of the...

  • Home
  • 824
  •  1
  •  2
Monthly Rent $2500 - $6300

Quaint romantic cottage with street parking, close to the beach & adventure! Key West, Florida, Listing ID: 26082

Whisk your special someone away for a tranquil retreat when you book your next vacation at this Key West cottage. Putting you right in the middle of the action while surrounding you with relaxation, this home offers room for two and street parking for convenience. Located...

  • Home
  • 500640
  •  1
  •  1
Monthly Rent $2500 - $6300

Cute dog-friendly tropical condo close to attractions w/a pristine shared pool Key West, Florida, Listing ID: 26085

This dog-friendly cottage includes street parking, a shared pool, and a location near Duval Street. Nestled in a quiet neighborhood about a mile from Higgs Beach Dog Park and a little under a mile to Mallory Square, you'll be able to get out and about with ease. With fresh...

  • Condo
  • 731
  •  10
  •  1 1/2
Monthly Rent $2100 - $6500

Charming cottage w/a private parking spot and private hot tub Key West, Florida, Listing ID: 26087

Trade in the daily grind for sugar-sand beaches and gentle ocean breezes when you book your getaway to this lovely Key West cottage. Featuring a private parking spot and a bubbling hot tub, stress won't stand a chance. Located just a mile from Fort Zachary Taylor Historic...

  • Home
  • 750
  •  2
  •  2
Monthly Rent $2400 - $6300

Dog-friendly seaside escape with shared pool, hot tub, tennis courts, and more! Key West, Florida, Listing ID: 26088

Bring your bathing suit, camera, and up to two canine companions (for a small nightly fee) for your next trip to this Key West cottage. With room for up to four guests, private parking, and resort amenities like a shared pool, hot tub, and tennis courts, fun will always be close...

  • Condo
  • 1178
  •  2
  •  2