Vacation Rentals with Pool in Long Key, FL: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Long Key

Refine your search

Price per night

Amenity Filter

Rating

85 Best Vacation Rentals with Pool in Long Key (Starting from $106)

Lime Tree Bay Resort
Lime Tree Bay Resort
Resort
Islamorada, FL, USA
0.7k from Long Key center

Accommodations, Pools, Resorts, Parking, Romantic, Pet-friendly, 3-star, Lodgings, Beach

61 Bedrooms54 Guests
8.6

Fabulous

2082 reviews

$247
Average price / night
Check Availability
Beautiful Pool Home Located in a Quiet Neighborhood
Beautiful Pool Home Located in a Quiet Neighborhood
House
Long Key, FL, 33001, United States
0.5k from Long Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
New to Booking
$649
Average price / night
Check Availability
Florida Keys Getaway with Stunning Ocean Views
Florida Keys Getaway with Stunning Ocean Views
House
Layton, FL, USA
4.3k from Long Key center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach

3 Bedrooms10 Guests
New to Booking
$909
Average price / night
Check Availability
3 Bedroom / 2.5 Bathroom Layton Home with Pool & Dockage
3 Bedroom / 2.5 Bathroom Layton Home with Pool & Dockage
House
Layton, FL, 33001, United States
0.6k from Long Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
New to Booking
$428
Average price / night
Check Availability
Ocean View Duplex Penthouse Retreat amenities: tennis court heated Pool Vista Key One
Ocean View Duplex Penthouse Retreat amenities: tennis court heated Pool Vista Key One
Apartment
Islamorada, FL, USA
9.0k from Long Key center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay

1 Bedroom10 Guests
New to Booking
$880
Average price / night
Check Availability
A fisherman's Dream, Ocean-front Condo.  Call Richard at 207-985-3600 to discuss
A fisherman's Dream, Ocean-front Condo. Call Richard at 207-985-3600 to discuss
Resort
Long Key, FL, 33001, United States
0.7k from Long Key center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
New to Booking
$246
Average price / night
Check Availability
Ocean View Penthouse Retreat amenities: tennis court heated Pool Vista Key Two
Ocean View Penthouse Retreat amenities: tennis court heated Pool Vista Key Two
Apartment
Islamorada, FL, USA
9.0k from Long Key center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$582
Average price / night
Check Availability
Private Waterfront Home, Heated Pool, Beach, Tiki w/Grill, Dock, Kayaks, Sunset
Private Waterfront Home, Heated Pool, Beach, Tiki w/Grill, Dock, Kayaks, Sunset
House
Long Key, FL, 33001, United States
0.8k from Long Key center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Extra Bed, Fireplace, Free Parking, Heater

3 Bedrooms10 Guests
10.0

Exceptional

103 reviews

$1473
Average price / night
Check Availability
Ocean View Two Duplex Penthouses Retreat amenities: tennis court heated Pool Vista Key
Ocean View Two Duplex Penthouses Retreat amenities: tennis court heated Pool Vista Key
Apartment
Islamorada, FL, USA
9.1k from Long Key center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Hot tubs, Places to stay

1 Bedroom18 Guests
New to Booking
$1388
Average price / night
Check Availability
Waterfront Wonder
Waterfront Wonder
House
Islamorada, FL, USA
9.9k from Long Key center

Accommodations, Pools, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Hot tubs

6 Bedrooms12 Guests
New to Booking
$1007
Average price / night
Check Availability
Home w/ 2nd Story Pool & Spa w/ Open Water Views
Home w/ 2nd Story Pool & Spa w/ Open Water Views
House
Layton, FL, 33001, United States
0.9k from Long Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

76 reviews

$1480
Average price / night
Check Availability
One Of A Kind Ocean Front With Boat Slip
One Of A Kind Ocean Front With Boat Slip
Condo
Layton, FL, 33001, United States
1.0k from Long Key center

AC, Balcony, Barbecue, Dryer, Elevator, Fireplace, Free Parking, Heater, Hot Tub

3 Bedrooms8 Guests
9.8

Exceptional

57 reviews

$383
Average price / night
Check Availability
Spectacular Views of Ocean with Pool and Boat Slip.
Spectacular Views of Ocean with Pool and Boat Slip.
House
Long Key, FL, 33001, United States
1.7k from Long Key center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$543
Average price / night
Check Availability
A Pirates Great Escape ~ 3bed/2baths  Ocean View Boat Slip included
A Pirates Great Escape ~ 3bed/2baths Ocean View Boat Slip included
House
Layton, FL, 33001, United States
2.0k from Long Key center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.8

Exceptional

21 reviews

$477
Average price / night
Check Availability
Fishing and Boating Paradise with 30 Foot Boat Slip and Swimming Pool
Fishing and Boating Paradise with 30 Foot Boat Slip and Swimming Pool
Condo
Long Key, FL, 33001, United States
2.1k from Long Key center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Free Parking, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

42 reviews

$426
Average price / night
Check Availability
Ocean front gated privacy with 3 bedrooms and protected boat slip.
Ocean front gated privacy with 3 bedrooms and protected boat slip.
Condo
Layton, FL, 33001, United States
2.3k from Long Key center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

57 reviews

$447
Average price / night
Check Availability
Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!
Escape to a Charming 2-Bedroom Cottage in Long Key – Your Perfect Getaway!
Cottage
Layton, FL, 33001, United States
3.7k from Long Key center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms8 Guests
4.0

Review score

1 reviews

$157
Average price / night
Check Availability
Gulf Front Rendezvous Retreat, Outdoor Resorts
Gulf Front Rendezvous Retreat, Outdoor Resorts
House
Long Key, FL, 33001, United States
3.7k from Long Key center

AC, Barbecue, Dryer, Internet, Kitchen, Living Area, No Smoking, Patio, Pool

2 Bedrooms6 Guests
New to Booking
$193
Average price / night
Check Availability
La Palma Verde at Outdoor Resorts
La Palma Verde at Outdoor Resorts
House
Layton, FL, 33001, United States
3.9k from Long Key center

AC, Barbecue, Dryer, Internet, Kitchen, Living Area, No Smoking, Patio, Pool

2 Bedrooms4 Guests
New to Booking
$193
Average price / night
Check Availability
Spacious 3BR Long Key Condo E8 with heated pool and stunning views!
Spacious 3BR Long Key Condo E8 with heated pool and stunning views!
Condo
Long Key, FL, 33001, United States
3.9k from Long Key center

AC, Balcony, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms7 Guests
New to Booking
$306
Average price / night
Check Availability
Outdoor Resorts, Long Key, FL
Outdoor Resorts, Long Key, FL
House
Layton, FL, 33001, United States
4.0k from Long Key center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Laundry, Microwave

2 Bedrooms8 Guests
6.8

Good

9 reviews

$106
Average price / night
Check Availability
BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!
BRING YOUR BOAT! Perfect Florida Keys Family Getaway with Activities Galore!
Cottage
Layton, FL, 33001, United States
4.0k from Long Key center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$280
Average price / night
Check Availability
Turtle Crawl on Long Key Oceanfront Beachfront with dock and pool
Turtle Crawl on Long Key Oceanfront Beachfront with dock and pool
House
Long Key, FL, 33001, United States
4.1k from Long Key center

AC, Balcony, Barbecue, Dryer, Internet, Kitchen, Laundry, Living Area, No Smoking

5 Bedrooms12 Guests
New to Booking
$2287
Average price / night
Check Availability
Pelican Retreat at Outdoor Resorts
Pelican Retreat at Outdoor Resorts
House
Long Key, FL, 33001, United States
4.1k from Long Key center

AC, Dryer, Internet, Kitchen, Living Area, Microwave, No Smoking, Pool, TV

2 Bedrooms6 Guests
New to Booking
$193
Average price / night
Check Availability
Florida Keys Getaway w/ Stunning Ocean Views
Florida Keys Getaway w/ Stunning Ocean Views
Apartment
65651 Overseas Hwy, Unit 17, Long Key, FL, 33001, United States
4.2k from Long Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area

New to Booking
$1045
Average price / night
Check Availability
Long Key florida,Beachfront Paradise, two bedroom ,3.5 bath, on Ocean, with Pool
Long Key florida,Beachfront Paradise, two bedroom ,3.5 bath, on Ocean, with Pool
Condo
Layton, FL, 33001, United States
4.2k from Long Key center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$394
Average price / night
Check Availability
Stunning 5BR open water view home in Long Key, perfect for groups of 10!
Stunning 5BR open water view home in Long Key, perfect for groups of 10!
House
Long Key, FL, 33001, United States
4.3k from Long Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
New to Booking
$1185
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Long Key.

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods

Stay Near Long Key's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Long Key Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 85 verified vacation rentals with a pool in Long Key. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Long Key vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $106 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Long Key offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Long Key welcome pets. Currently, 25 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Long Key often include additional outdoor features such as Pool, Kitchen, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Long Key offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.