Apartment • 28 People • 13

• 10

•

From

11,213 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 11,213 USD /Night (minimum stay 1 night)

WiFi

Colorado Charm

This unique Colorado home is ideal for large gatherings, whether it’s a family reunion or a company retreat. Set on 30 acres, this estate offers an impressive collection of accommodations, including the main house, two villas, and three cabins – there’s room for everyone. You can look forward to breathtaking 360º views of the Rocky Mountains, a 1-acre lake stocked with large trout, and a swimming beach and dock. Little ones will delight in the three-story treehouse, while big kids will appreciate the shuffleboard courts, corn hole, basketball, and tetherball. After long days spent hiking, a starlit soak in the hot tub will surely appeal to all. *There’s free parking at this home. We recommend bringing cars to get the most out of your stay. *This home is spread over the main house, two villas and three cottages, so you won’t all be sleeping under the same roof. *At full occupancy, twelve guests will sleep on six sofa beds. *Your ho...More Details

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Tallahassee FL, Apartment for rent

Apartment • 12 People • 7

• 9

•

From

9,938 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 9,938 USD /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Coastal Rhapsody

If you’re in search of a coastal adventure or a relaxing beachfront escape, this home delivers the perfect solution. Nestled in Stonington village, you’ll be spoiled by beautiful views, an expansive two acres of lush grounds, a private pool and a tennis court. And while there’s everything you could need to enjoy the great outdoors, the rooms are just as inviting with a home theatre, a sauna, a wine cellar and plenty of socialising space across the living and dining rooms. You might find it hard to leave this peaceful sanctuary, but it’s just a short stroll to the nearest restaurants and shops. *Private parking is available here. *This home includes direct beach access. If you’re travelling with little ones, they will need to be supervised outside at all times. *Your host can provide a cot for free on request. *Complimentary toiletries are provided for you here. *The host kindly asks guests to observe quiet hours from 10pm to 8am....More Details

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Broward County, House for rent

House • 12 People • 6

• 5

•

From

8,374 USD /night

Min Stay 1 night

Broward County, USA

$ 8,374 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Surf's Horizon

On one of Fort Lauderdale’s serene waterways, guests here have access to a shared dock to explore by paddleboard, boat or kayak. There’s also a shared swimming pool and barbecue area within the complex. The home is made up of four self-contained suites, each with its own kitchen and living room. The main unit has a glorious mid-century-style living room and gourmet kitchen, plus a dedicated office for those working remotely. A private terrace provides a spot for al fresco feasts, particularly atmospheric at sunset when the sky streaks mauve. It's a short drive to Fort Lauderdale's beaches and beach chairs, a cooler and a beach cart are provided. *This home consists of four self-contained suites, each with its own kitchen or kitchenette and living room.\n*The swimming pool, dock and barbecue area are shared with other apartments within the complex.\n*Beach gear like chairs, a cooler and a beach cart are provided and guests have access ...More Details

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Tallahassee FL, House for rent

House • 18 People • 8

• 8

•

From

5,794 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 5,794 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Marina Living

Welcome home to this stunning 8-bedroom villa in the heart of Lunara Bay, Key West. This luxurious retreat is perfect for families and large groups, offering spacious interiors, a large pool, and lush outdoor areas. Enjoy beautifully designed living spaces, relax by the pool, or explore the nearby attractions. With an exclusive marina for boats up to 40-foot, it's the ideal base for an unforgettable getaway. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *There's no lift here. You'll need to be able to climb stairs to reach the floors of the home. *The Florida Keys are a notoriously difficult place to navigate, but you are welcome to dock in the exclusive marina, which accommodates boats up to 40 feet in length. Please note there's no power or pump-out service to the slips, and there's a maximum of one boat per slip. *There’s free parking for up to four cars on the drivewa...More Details

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Tallahassee FL, House for rent

House • 35 People • 8

• 9

•

From

5,775 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 5,775 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Pocono Mansion

Escape the everyday and make unforgettable memories at this 174-acre luxury mansion nestled in the beautiful Pocono Mountains. Whether you’re planning a relaxing weekend getaway with a large group of friends or that long overdue family reunion, this home has all the space and on-site entertainment you need to have fun and rejuvenate in peaceful surroundings. With so much to do at the mansion, adventure starts at home. Take a dip in the private pool and unwind in the luxurious hot tub before enjoying a private screening in the home cinema room. When you're all chilled out, why not rally up some healthy competition with a game of tennis, trade workout tips in the gym, or play in the games area? Relax in the modern and minimalist interior and lay on a feast for everyone at the large dining table, or gather outside for some fabulous alfresco meals. If you venture out, explore the scenic beauty of the Pocono mountains and admire the pre...More Details

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Tallahassee FL, House for rent

House • 14 People • 6

• 6

•

From

5,750 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 5,750 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Dream Escape

Step off the dock and straight into holiday mode — this waterfront retreat is made for easygoing island days. Set in a gated community with its own private marina, you can moor your boat just steps from the door. Back at the house, there’s a private pool for lazy afternoons, a barbecue for garden grilling, and free access to the estate gym. Inside, it’s all bright spaces and breezy vibes, with a breakfast bar, a big table for family feasts, and a bunk-bed room the kids will love. When adventure calls, local seafood spots and watersports are all within easy reach. *One bedroom has two twin bunk beds and no door — it’s not the most private space, but perfect for little ones. *You’ll have access to a private dock that accommodates one boat up to 40’ — just note there's no power or pump-out service, and navigating the Florida Keys can be tricky. *There’s space to park up to four vehicles and a boat trailer on the driveway. *This home is i...More Details

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Miami FL, Apartment for rent

Apartment • 13 People • 6

• 6

•

From

5,688 USD /night

Min Stay 1 night

Miami FL, USA

$ 5,688 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Oasis Spring

Step over the koi pond and arrive inside a realm of soothing sounds, luscious greenary and a home filled with luxurious home comforts. In the heart of Miami Shores, this sleek and contemporary villa offers a relaxing stay that transitions indoor living through to its oasis-like garden outside. Marble floors, natural wood accents and Balinese designs present a tranquil setting, just a few minutes drive away from the Wynwood area –known as the arts hub of South Florida. Whereby colourful murals, street art and numerous galleries and museums enhance the vibrant neighbourhood, amidst dozens of restaurants and cafes – that's if you can tear yourself away from your private haven at home. At the villa, relax in the Florida sunshine out on the sun-kissed terrace, before cooling off in the pool. The more energised members of the group might enjoy a game of ping pong or basketball under the palms as the sun lowers in the sky. When evening comes, ...More Details

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Tallahassee FL, House for rent

House • 14 People • 6

• 6

•

From

5,658 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 5,658 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Paradise Key

Discover the magic of Florida from this impressive home in Key West. Outside, you can relax and unwind by the private heated pool. There’s a family-friendly yard and a fire pit for magical evenings under the stars. Inside, the rooms are just as inviting with plenty of space to socialise and stretch out across the six bedrooms. Guests can enjoy access to the communal gym and there’s a dock for boats. Plus, your host can help organise a range of extra services – including tailored experiences and chauffeurs. And when it comes to explorations further afield, you'll find all the attractions of Key West within easy reach – including restaurants and bars. *This home is located in a gated community with a communal gym. Guests also have access to the marina which can accommodate one boat per slip – size restrictions apply so check with your host for more information. *Private parking is available for up to three cars and a boat trailer. *Pl...More Details

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Tallahassee FL, House for rent

House • 14 People • 6

• 6

•

From

5,647 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 5,647 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Marina Nights

This home has bagged itself a great location in a gated community, less than a mile from ever-popular Key West. With a private pool, alfresco dining area, and fire pit, outdoor living is easy here. Keen sailors can bring their boat and dock it at the on-site marina, and there’s plenty of room in the driveway for your boat trailer. If you’re feeling active, check out the gym at the nearby fitness centre. Or if you want a more relaxing experience, your host can arrange a private chef to cook for you in the home. We think this place is a great option for those wanting to experience Florida Keys with a touch of luxury. *The swimming pool isn't fenced. If you're bringing little ones, they'll need to be supervised at all times. *The bunk bed bedroom doesn’t have a door – this room is best suited to children. *If you're travelling with little ones, your host can provide a high chair for free. You'll need to request it in advance. *There’s o...More Details

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Tallahassee FL, House for rent

House • 16 People • 6

• 6

•

From

5,647 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 5,647 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Theodore

This home offers an idyllic retreat in Key West. Outside, you can savour blissful days by the heated pool and there's a fire-pit for magical evenings under the stars. Head inside and you'll find the rooms are just as welcoming with plenty of chill-out space and six bedrooms – all of which come with en-suite bathrooms for optimum privacy. Exercise enthusiasts will appreciate the communal gym and if you happen to have a boat you can dock it in the marina. It’s also less than a mile to the heart of Key West and the nearest restaurants. *This home is located in a gated community with a communal gym. Guests also have access to the marina which can accommodate boats up to 40’ in length. Please note there is a maximum of one boat per slip. *Private parking is available for up to two cars and a boat trailer. *Please note the fans in the bedrooms only operate with the light on. *Complimentary toiletries are provided for your stay. Air Con...More Details

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Sarasota-County, Apartment for rent

Apartment • 19 People • 8

• 7

•

From

5,618 USD /night

Min Stay 1 night

Sarasota-County, USA

$ 5,618 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Siesta Dream

This nearly beachfront, Siesta Key luxury rental home features views of Siesta Key Beach and the Gulf of Mexico from multiple levels and the rooftop deck. This Siesta Key luxury rental is just steps to Siesta Key Beach and only a 3-minute walk to Siesta Key Village. This luxury vacation rental on Siesta Key also has a trolley stop nearby as well for another mode of free transportation. The location simply cannot be beat. This home offers approximately 4,800 square feet of interior living space and 3,000+ square feet of outdoor covered patios, balconies, pool areas, and entertainment space. - Access to Beach Accessible Parking Air Conditioning Balcony Barbeque Bathtub Beach Essentials Bicycles Black-Out Blinds Blender Board Games Carbon Monoxide Detector Ceiling Fans Central Heating Coffee Maker Cooking Essentials Dishwasher Dryer Fire Extinguisher First Aid Kit Free Parking Free Parking On Premises Freezer Fridge Games Console Garde...More Details

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Tallahassee FL, House for rent

House • 16 People • 6

• 6

•

From

5,565 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 5,565 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Pearl of Key West

Spend your days soaking up the island breeze at this laid-back retreat just outside Key West. Tucked inside a quiet gated community, this spacious six-bedroom home is made for group getaways, with a private boat slip, breezy balconies, and enough room for everyone to spread out. The vibrant streets of Old Town are just a few minutes away by car, bike, or golf cart if you're feeling adventurous. Or, you can take it easy, dipping in the pool, or firing up the grill for a sunset dinner. Thoughtful touches like free gym access makes island life feel like a home-from-home. *You'll have complimentary access to FYT, a nearby gym. *There’s free parking for up to four cars and a boat trailer on the driveway. *The private dock can accommodate one boat up to 40 feet, but there is no power or pump-out service provided. Navigating the Florida Keys can be tricky, so local boating knowledge is advised. *The ceiling fans in each bedroom only work whe...More Details

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Tallahassee FL, Apartment for rent

Apartment • 14 People • 6

• 6

•

From

5,302 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 5,302 USD /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

The Berkshires Splendour

Nature meets luxury at this stunning Berkshire Mountain retreat. Just twenty minutes from Great Barrington and with hiking trails all around, this home is an idyllic escape from the hustle and bustle. Set in 167 private acres, this home has everything you could wish for. Admire mountain views from the hot tub on the sun deck, unwind in the steam room, and enjoy a tipple from the main bedroom’s wine bar. Your host can arrange for a chef to whip up feasts in the chef’s kitchen and order custom kegs for the kegerator. The open-concept living areas – with floor-to-ceiling windows – make socialising a dream. This home is perfect for a large family gathering. *There’s a two-car heated garage here. *Your host can provide a pack and play cot and a high chair for little ones. *While not every bedroom or bathroom has been photographed, we expect the style and standard to be consistent with the rest of the home. *Bedroom six is equipped with th...More Details

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Tallahassee FL, Apartment for rent

Apartment • 24 People • 8

• 7

•

From

5,281 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 5,281 USD /Night (minimum stay 1 night)

Swimming Pool

Air Conditioning

WiFi

Large Glass of Red

Just outside of the village of Calistoga in the northernmost tip of the Napa Valley, you'll encounter this rustic yet refined retreat surrounded by acres of verdant vineyards and lush gardens. With no nearby neighbours, enjoy that all-too-rare feeling of seclusion, yet the convenience of only being a mile and a half from downtown Calistoga. The estate is divided across three adjacent villas – which helps maintain privacy for large family get-togethers and groups of friends – while there's a yurt on the grounds that makes for an adventurous option for the kids. Everything here is set up for outdoor living. There are no fewer than twelve sets of French doors leading out onto ~1,000 sq ft of balconies and ~2,000 sq ft of patio space. The large outdoor gazebo boasts a full outdoor kitchen with a serious gas barbecue and alfresco dining area overlooking the stunning pool and Jacuzzi area. In addition to the usual high-end outdoor amenities, ...More Details

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Tallahassee FL, House for rent

House • 16 People • 5

• 5

•

From

4,950 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 4,950 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Key Lime Delight

Just minutes from the heart of Key West, this home is a laid-back waterfront escape with room for the whole crew. Five bedrooms, including a playful bunk room, make this home ideal for families and groups, while the open-plan layout keeps everyone connected. There’s a private pool, gated yard, and your own dock outside – perfect for boaters, sun-seekers and four-legged friends alike. With free access to a nearby gym and plenty to see in the local area, it’s your gateway to easy living in the Keys. *You'll have complimentary access to FYT, a nearby gym. *There’s free parking for up to four cars and a boat trailer on the driveway. *The private dock can accommodate one boat up to 50 feet, but there is no power or pump-out service provided. Navigating the Florida Keys can be tricky, so local boating knowledge is advised. *At full occupancy, two guests will be sleeping on the sofa bed in the living area, and on the top of bunk beds, which...More Details

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Hudson Valley FL, Cottage for rent

Cottage • 10 People • 4

• 3

•

From

4,887 USD /night

Min Stay 1 night

Hudson Valley FL, USA

$ 4,887 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Hawk - Falcon

Unplug, tune out and drop off the grid for a while. Nestled out of the way in the Rondout Valley in Upstate New York, this secluded barn house and cottage combo is perfect for anyone looking to get away from it all. Sat within seventy-five acres of idyllic woodland, the scene is set for you to live out your Captain Fantastic fantasies. There's even a renovated bus to sleep in (available to rent separately). Host Casey has built fairytale hangouts to immerse you in nature, including a hammock overlooking a waterfall, a gazebo beside a lily pond, and a yoga platform in the woods. The barn decking and outdoor kitchen adorned with fairy lights is a magical spot for family meals. Entertaining the family is easy with fireside songs (your hosts recommend making s'mores with Tate's Cookies instead of Graham Crackers – you can thank them later), swims in the pool and indoor and outdoor games for all ages to enjoy. We fully envision your kids dau...More Details

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Broward County, Apartment for rent

Apartment • 16 People • 8

• 8

•

From

4,852 USD /night

Min Stay 1 night

Broward County, USA

$ 4,852 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Sunshine Magic

This show-stopper of a home is ideal for large groups. It’s spread over three floors with a lift to make it more accessible, and there’s heaps of room for everyone to gather together. We love the two-level living botanical greenhouse, which is a wonderful spot for special events. The home sits on the waterfront with a dock, so as you soak up the sun in the heated pool or hot tub you can watch boats pass by. There’s a sense of exclusivity here, yet there’s something to appeal to everyone, from the wine cellar to the sports bar. *Your host can provide four beach chairs, a cooler, and a beach cart. \n*The minimum booking age for this home is 25 unless approved by your host before booking.\n*Your host kindly asks you to respect the quiet hours outside from 10pm-7am.\n*There’s a security camera at the front of the home, and a sound-level monitoring system.\n*The second and third floors of this home can be accessed via a glass lift, as well...More Details

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Tallahassee FL, House for rent

House • 14 People • 5

• 5

•

From

4,838 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 4,838 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Key Sunset

If you’ve ever dreamed of a tropical getaway in the sun, with palm trees swaying and crystal blue waters visible from the kitchen window, this is the place for you. Located in the iconic Key West, this five-bedroom home offers every comfort you’d expect from a Floridian home right on the water – including a fenced pool, a spacious and fully-equipped kitchen, and even your own private dock extending into the sea. With complimentary gym access, keyless entry and plenty of room to relax, this remarkable home is a true gem in the Florida Keys. *At full occupancy, two guests will be sleeping on the sofa bed in the living area, and two on the day beds in the fifth bedroom. *Your host encourages the use of the private dock, however please note that it can only accommodate one boat at a time, up to 50 feet in length. The host recommends that only skilled boaters use it, as the water around Florida Keys is notoriously difficult to navigate. T...More Details

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Tallahassee FL, House for rent

House • 10 People • 4

• 4

•

From

4,590 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 4,590 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

Moonlit Bay

Just beyond the buzz of Key West, this waterfront villa offers easy-going luxury in a gated community. Outside you can relax in the private pool, fire up the barbecue, or jet off from the private slip. The fenced garden is perfect for kids and pets to roam happily, while complimentary gym access and local dining spots are just minutes away. Whether you’re cruising the Keys or soaking up the sun at home, this spot blends laid-back comfort with everything you need for an unforgettable island escape. *You'll have complimentary access to FYT, a nearby gym. *There’s free parking for up to four cars and a boat trailer on the driveway. *The private dock can accommodate one boat up to 50 feet, but there is no power or pump-out service provided. Navigating the Florida Keys can be tricky, so local boating knowledge is advised. *At full occupancy, two guests will be sleeping on the sofa bed in the living area. *Please note that the home is eleva...More Details

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Tallahassee FL, House for rent

House • 12 People • 4

• 4

•

From

4,534 USD /night

Min Stay 1 night

Tallahassee FL, USA

$ 4,534 USD /Night (minimum stay 1 night)

Swimming Pool

Pets Allowed

Air Conditioning

WiFi

The Tidal Flow

Set beside the water in a quiet gated community, this Key West retreat is all breezy days and golden-hour swims. Coastal tones and soft natural light bring a sense of calm throughout, while outside, the private pool, dock, and fenced garden make it easy to unwind. Start your mornings with coffee on the terrace, then take to the water or stretch out with a yoga mat in the sun. Inside, the open-plan living space is perfect for lazy lunches, slow dinners, and long conversations. There’s a Peloton for active days, high-speed Wi-Fi for staying connected, and parking for four vehicles. A gym pass is included, and with beaches, boat ramps and island favourites close by, the best of the Keys is within easy reach. *The home is accessed via stairs only—there’s no lift, and it’s elevated above sea level. *Children and pets should be supervised near the pool and waterfront dock. *Please note that the ceiling fans in the bedrooms only operate when...More Details

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Luxury Rentals Florida Holiday rentals American vacation rentals of Apartments and Houses - Short term lettings

Found 809 Florida holiday homes for rent

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Tallahassee FL, USA

Broward County, USA

Tallahassee FL, USA

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