Heated Pool, Tiki Hut, Huge Yard, Bar, Walk 2 Ave
Heated Pool, Tiki Hut, Huge Yard, Bar, Walk 2 Ave
Heated Pool, Tiki Hut, Huge Yard, Bar, Walk 2 Ave
Heated Pool, Tiki Hut, Huge Yard, Bar, Walk 2 Ave
Heated Pool, Tiki Hut, Huge Yard, Bar, Walk 2 Ave

Heated Pool, Tiki Hut, Huge Yard, Bar, Walk 2 Ave

3 bedrooms·2 baths
Delray Beach • Florida

$1,089.32 USD total for 3 nights

Oct 5 – 8, 2026

Tiki Hut, Htd Pool, Bar & Putting Greens Near Atlantic Avenue
Tiki Hut, Htd Pool, Bar & Putting Greens Near Atlantic Avenue
Tiki Hut, Htd Pool, Bar & Putting Greens Near Atlantic Avenue
Tiki Hut, Htd Pool, Bar & Putting Greens Near Atlantic Avenue
Tiki Hut, Htd Pool, Bar & Putting Greens Near Atlantic Avenue

Tiki Hut, Htd Pool, Bar & Putting Greens Near Atlantic Avenue

3 bedrooms·2 baths
Delray Beach • Florida

$1,230.57 USD total for 3 nights

Oct 5 – 8, 2026

Pull up a chair, catch up with family and friends
Delight in an outdoor bite, before heading out to get your vitamin SEA🌊
King bed, 100% cotton linens, back patio view
Relax in the shade or in the sun, on the back patio, with access from the master bedroom
Master suite, with luggage rack, flat screen TV, and back patio access

Coastal Cottage

2 bedrooms·2 baths
Delray Beach • Florida
5(7 reviews)

$1,822.86 USD total for 4 nights

Oct 16 – 20, 2026

Welcome to Seaside Escape!
Only 1000 feet to the beach!!
Breakfast bar with seating for 2
Dining table with bench seating, expandable table and extra chairs
Top of the line appliances

Seaside Escape

2 bedrooms·2 baths
Delray Beach • Florida
5(17 reviews)

$1,769.04 USD total for 4 nights

Sep 29 – Oct 3, 2026

Spacious living area, sink right into comfort on the large leather sectional
Only 1000 feet to the beach!
Ocean Pearl, Delray Beach
Luxe King mattres, cotton linens, ambient lighting
Dining table for 4 with a courtyard view

Ocean Pearl, Delray Beach

1 bedroom·1 bath
Delray Beach • Florida
5(5 reviews)

$950.04 USD total for 3 nights

Sep 29 – Oct 2, 2026

Spacious Designer Home Htd Pool Near Atlantic Ave
Spacious Designer Home Htd Pool Near Atlantic Ave
Spacious Designer Home Htd Pool Near Atlantic Ave
Spacious Designer Home Htd Pool Near Atlantic Ave
Spacious Designer Home Htd Pool Near Atlantic Ave

Spacious Designer Home Htd Pool Near Atlantic Ave

4 bedrooms·2 baths
Delray Beach • Florida

$1,553.75 USD total for 3 nights

Oct 18 – 21, 2026

Welcome to Paradise Breezes and Paradise Cottage House. Your 4 bedroom (3 Kings-1 Queen) 3.5 bathroom, heated pool home awaits!
Dining Room with seating for 8
King primary suite, second floor, pool view, balcony access, new flooring
Well stocked, spacious chef's kitchen in the main house.
Expansive, tropical courtyard pool area with options for lots of sun or shade

Paradise Breezes & Cottage House

4 bedrooms·3½ baths
Delray Beach • Florida
5(12 reviews)

$3,022.12 USD total for 3 nights

Sep 29 – Oct 2, 2026

Ahhhhh...Peaceful and Serene
Fully equipped kitchen
Relax on the large cloud!
Enjoy your private backyard loungng by the pool
Drone view

Tropic Paradise

3 bedrooms·2 baths
Delray Beach • Florida
5(28 reviews)

$3,257.28 USD total for 4 nights

Sep 29 – Oct 3, 2026

Luxe Heated Pool Home, Tiki Hut, Bar, Air Hockey!
Luxe Heated Pool Home, Tiki Hut, Bar, Air Hockey!
Luxe Heated Pool Home, Tiki Hut, Bar, Air Hockey!
Luxe Heated Pool Home, Tiki Hut, Bar, Air Hockey!
Luxe Heated Pool Home, Tiki Hut, Bar, Air Hockey!

Luxe Heated Pool Home, Tiki Hut, Bar, Air Hockey!

3 bedrooms·2 baths
Delray Beach • Florida

$985.36 USD total for 3 nights

Sep 29 – Oct 2, 2026

An aerial view of the outdoor oasis, with a huge patio area, hot tub, sun loungers, outdoor dining table, BBQ, decking along the canal edge and of course the pool and hot tub - what more could you want?
Welcome to your next stunning waterfront Delray retreat! Starting off in the stunning outdoor private pool and dock area. Make use of the hot tub with your loved or perhaps the loungers in the shallow pool area - your private paradise
With sun loungers around the pool with small tables between, bring out your cocktails and snacks and enjoy every moment. Take a dip in the hot tub and feel the relaxation of the jet streams as the air is filled with laughter and happiness.
At night the pool and hot tub come alive with the LED lights creating a beautiful spectacle, how about a night time swim in the bright blue water!? Or change the LED light color setting to cycle through a variety of 10+ colors!
Take a seat on the outdoor dining table to enjoy your BBQ treats or perhaps a hot meal made from the fully equipped kitchen. With seating for 6 and an umbrella to block the mid day sun during your delicious meal time on the private patio.

Waterfront, Spa, Htd Pool, Billiards, Lanai, Canal

4 bedrooms·2 baths
Delray Beach • Florida

$1,531.15 USD total for 3 nights

Oct 18 – 21, 2026

Heated Pool, Big Deck, Billiards, Games, PAC-MAN
Heated Pool, Big Deck, Billiards, Games, PAC-MAN
Heated Pool, Big Deck, Billiards, Games, PAC-MAN
Heated Pool, Big Deck, Billiards, Games, PAC-MAN
Heated Pool, Big Deck, Billiards, Games, PAC-MAN

Heated Pool, Big Deck, Billiards, Games, PAC-MAN

4 bedrooms·2 baths
Delray Beach • Florida

$1,107.40 USD total for 3 nights

Sep 29 – Oct 2, 2026

Tiki Hut, Htd Pool, Billiards, Putt-Putt, Canal
Tiki Hut, Htd Pool, Billiards, Putt-Putt, Canal
Tiki Hut, Htd Pool, Billiards, Putt-Putt, Canal
Tiki Hut, Htd Pool, Billiards, Putt-Putt, Canal
Tiki Hut, Htd Pool, Billiards, Putt-Putt, Canal

Tiki Hut, Htd Pool, Billiards, Putt-Putt, Canal

3 bedrooms·2 baths
Delray Beach • Florida

$1,162.77 USD total for 3 nights

Oct 4 – 7, 2026

Water Front, Fishing dock
Tanning ledge.. salt water pool: covered pool enclosure
Large SW pool. Heated during the winter
Screened in pool patio keeps the bugs out
Close to the beaches

Classy N Cozy Delray Beach pool home

3 bedrooms·2 baths
Delray Beach • Florida

$1,492.47 USD total for 3 nights

Oct 31 – Nov 3, 2026

Waterfront Htd Pool, Putt-Putt Pergola, Air Hockey
Waterfront Htd Pool, Putt-Putt Pergola, Air Hockey
Waterfront Htd Pool, Putt-Putt Pergola, Air Hockey
Waterfront Htd Pool, Putt-Putt Pergola, Air Hockey
Waterfront Htd Pool, Putt-Putt Pergola, Air Hockey

Waterfront Htd Pool, Putt-Putt Pergola, Air Hockey

4 bedrooms·2 baths
Boynton Beach • Florida

$1,139.04 USD total for 3 nights

Oct 3 – 6, 2026

Private Heated Pool, Lanai, Billiards & Ping Pong
Private Heated Pool, Lanai, Billiards & Ping Pong
Private Heated Pool, Lanai, Billiards & Ping Pong
Private Heated Pool, Lanai, Billiards & Ping Pong
Private Heated Pool, Lanai, Billiards & Ping Pong

Private Heated Pool, Lanai, Billiards & Ping Pong

4 bedrooms·2 baths
Boynton Beach • Florida

$1,107.40 USD total for 3 nights

Oct 4 – 7, 2026

Welcome to your Delray Beach Wanderlust Luxuries Home! Fully fenced in landscaped property, surrounded by beautiful clusias.
Staying in for the night? Enjoy the spacious living room with your family or friends, relaxing on the luxurious leather couch equipped with 3 recliners.
Welcome to your fully stocked kitchen! Whether you love to cook, or would rather order in, you are all set to just arrive and enjoy yourself!
Our dining room table expands to fit 12 comfortably spaced out with the two long side benches. What's for dinner?
Whether it's raining or you're just feeling competitive, the game room is a perfect hangout spot!

BohoChic Luxury Home minutes to Atlantic Ave&Beach

3 bedrooms·2 baths
Delray Beach • Florida
5(13 reviews)

$2,282.75 USD total for 6 nights

Sep 29 – Oct 5, 2026

Waterfront w/ Htd Pool, Tiki Hut, Billiards, & Bar
Waterfront w/ Htd Pool, Tiki Hut, Billiards, & Bar
Waterfront w/ Htd Pool, Tiki Hut, Billiards, & Bar
Waterfront w/ Htd Pool, Tiki Hut, Billiards, & Bar
Waterfront w/ Htd Pool, Tiki Hut, Billiards, & Bar

Waterfront w/ Htd Pool, Tiki Hut, Billiards, & Bar

4 bedrooms·2 baths
Boynton Beach • Florida

$1,391.03 USD total for 3 nights

Oct 27 – 30, 2026

Boynton Blue Ocean 3br w/office 7 min to the beach
Boynton Blue Ocean 3br w/office 7 min to the beach
Boynton Blue Ocean 3br w/office 7 min to the beach
Boynton Blue Ocean 3br w/office 7 min to the beach
Boynton Blue Ocean 3br w/office 7 min to the beach

Boynton Blue Ocean 3br w/office 7 min to the beach

3 bedrooms·2 baths
Boynton Beach • Florida
5(6 reviews)
$350/ night(excl. fees & taxes)
Listing image 1
5-Bed Home with Pool & Mini Golf in Boynton Beach
Backyard oasis with pool, private putting green, hammock and palms
5-Bed Home with Pool & Mini Golf in Boynton Beach
5-Bed Home with Pool & Mini Golf in Boynton Beach

5-Bed Home with Pool & Mini Golf in Boynton Beach

5 bedrooms·3 baths
Boynton Beach • Florida
5(1 review)

$1,824.75 USD total for 3 nights

Sep 29 – Oct 2, 2026

HEATED Swimming Pool & Deluxe Hot Tub {Completely Screened to Repel Bugs, Etc.}
HEATED Swimming Pool & Deluxe Hot Tub {100% Privacy with Drapes & Roll-Down Shades}
Deluxe Hot Tub with Waterfall & Colored LED Lights Overlooks Tiki Garden
Screened Pool Area, with Full Sun Exposure for Tanning, & Fenced Back Yard
Another Outdoor Seating Area with Lovely Pool View

Private Tropical Home w/ HEATED Pool & Hot Tub!!!*

3 bedrooms·2 baths
Boynton Beach • Florida
5(7 reviews)

$3,696.50 USD total for 6 nights

Oct 4 – 10, 2026

"Hawaii" Bedroom {Glass Door has Built-In Blinds & Pull-Down Shade}
HEATED Swimming Pool & Deluxe Hot Tub {Completely Screened to Repel Bugs, Etc.}
HEATED Swimming Pool & Deluxe Hot Tub {100% Privacy with Drapes & Roll-Down Shades}
Deluxe Hot Tub with Waterfall & Colored LED Lights Overlooks Tiki Garden
Screened Pool Area, with Full Sun Exposure for Tanning, & Fenced Back Yard

2-Bedroom Tropical Suite w/ HEATED Pool & Hot Tub!

2 bedrooms·1 bath
Boynton Beach • Florida
5(4 reviews)

$947.50 USD total for 3 nights

Oct 4 – 7, 2026

Peaceful Lake View Vacation Home with Heated Pook
Peaceful Lake View Vacation Home with Heated Pook
Peaceful Lake View Vacation Home with Heated Pook
Peaceful Lake View Vacation Home with Heated Pook
Peaceful Lake View Vacation Home with Heated Pook

Peaceful Lake View Vacation Home with Heated Pook

3 bedrooms·3 baths
Boynton Beach • Florida

$1,140.00 USD total for 3 nights

Oct 2 – 5, 2026

Fabulous 3 bedroom home with huge pool and garden image 1
Fabulous 3 bedroom home with huge pool and garden image 2
Fabulous 3 bedroom home with huge pool and garden image 3
Fabulous 3 bedroom home with huge pool and garden image 4
Fabulous 3 bedroom home with huge pool and garden image 5

Fabulous 3 bedroom home with huge pool and garden

3 bedrooms·2 baths
Lake Worth • Florida

$927.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

The living room at Pink Posh Inn doesn’t do subtle — fuchsia velvet sofa, teal accent chairs, a vibrant medallion rug, and floor-to-ceiling black drapes for the ultimate movie night. Step outside and the pool is waiting.
Pool glowing, fire pit burning, string lights strung across a South Florida sky at dusk. Pull up a chair.
Where every evening feels like a reservation worth keeping.
From the moment you arrive, Pink Posh Inn feels like a place you’ve always wanted to come home to.
Fully stocked kitchen with induction cooktop, convection oven, and LG refrigerator with craft ice maker. Note: flowers, candles, and food shown are photo styling only and not provided.

Pool Oasis, 5 minutes to beach

3 bedrooms·3 baths
Lake Worth • Florida

$942.50 USD total for 3 nights

Sep 29 – Oct 2, 2026